dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb5340bf9e12420f961f85565674a2d1 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccc(F)c(Cl)c1>>N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1 | O.ClC1=C(C=CC(=C1)[N+](=O)[O-])F.OC=1C=C(C#N)C=CC1.C([O-])([O-])=O.[K+].[K+]>>ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)[N+](=O)[O-] | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:19]1.F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[Cl:18]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[Cl:18])[cH:19]1 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccc(F)c(Cl)c1 | N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 91.9 | [{"value": 91.9, "product": "ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of 2-chloro-1-fluoro-4-nitrobenzene (3.7 g) and 3-hydroxybenzonitrile (2.5 g) in N,N-dimethylformamide (50 mL) was added potassium carbonate (4.4 g), and the mixture was stirred at 60° C. for 4 hrs. After the completion of the reaction, water (50 mL) was added, and the mixture was stirred for 10 min. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C=O)C | 60 | 4 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccc(F)c(Cl)c1>CN(C=O)C>N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a1d4a4e58c14dbb8c71ddea5d96011e | N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1>>N#Cc1cccc(Oc2ccc(N)cc2Cl)c1 | ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-]>>NC1=CC(=C(OC=2C=C(C#N)C=CC2)C=C1)Cl | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:17]2)[c:15]([Cl:16])[cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]2[Cl:16])[cH:17]1 | N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1 | N#Cc1cccc(Oc2ccc(N)cc2Cl)c1 | null | null | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 70.2 | [{"value": 70.2, "product": "NC1=CC(=C(OC=2C=C(C#N)C=CC2)C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 10 | MINUTE | To a solution of 3-(2-chloro-4-nitrophenoxy)benzonitrile (2.0 g) in ethanol/water (9:1, 40 mL) was added calcium chloride (90%, 449 mg), and the mixture was stirred at 100° C. for 10 min. Reduced iron (90%, 2.7 g) was added at room temperature, and the mixture was stirred at 100° C. for 5 hrs. After the completion of t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O.O | 100 | 0.166667 | N#Cc1cccc(Oc2ccc([N+](=O)[O-])cc2Cl)c1>C(C)O.O>N#Cc1cccc(Oc2ccc(N)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0af3ceb8b6bd4b00a89823f37bb0fddb | CCO.O=C(O)c1cc([N+](=O)[O-])ccc1F>>CCOC(=O)c1cc([N+](=O)[O-])ccc1F | S(=O)(Cl)Cl.FC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].C(C)O>>FC1=C(C(=O)OCC)C=C(C=C1)[N+](=O)[O-] | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][c:14]1[F:15] | CCO.O=C(O)c1cc([N+](=O)[O-])ccc1F | CCOC(=O)c1cc([N+](=O)[O-])ccc1F | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 80 | CELSIUS | 4 | HOUR | Under ice-cooling, thionyl chloride (8.02 mL) was added dropwise to ethanol (200 mL), and 2-fluoro-5-nitrobenzoic acid (13.81 g) was added. This mixture was stirred at 80° C. for 4 hrs. and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | 80 | 4 | CCO.O=C(O)c1cc([N+](=O)[O-])ccc1F>>CCOC(=O)c1cc([N+](=O)[O-])ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1755d888fa243c2bda0a67feb7d57c2 | CCOC(=O)c1cc([N+](=O)[O-])ccc1F.Oc1ccccc1>>CCOC(=O)c1cc(N)ccc1Oc1ccccc1 | FC1=C(C(=O)OCC)C=C(C=C1)[N+](=O)[O-].C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+]>>NC=1C=CC(=C(C(=O)OCC)C1)OC1=CC=CC=C1 | O=[N+:9]([O-])[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12](F)[cH:11][cH:10]1.[OH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:10][cH:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CCOC(=O)c1cc([N+](=O)[O-])ccc1F.Oc1ccccc1 | CCOC(=O)c1cc(N)ccc1Oc1ccccc1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | fcde22d25a281822013269b17d8b3414bea830a4bf58d8806a9dfee8028580dd | 62abf9f7921a98ccae96c82f80f078cf7b92f589fff664adf63edbf966dddb72 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[c:7]1:[c:6]:[c:4](-[NH2;D1;+0:5]):[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | 82.9 | [{"value": 82.9, "product": "NC=1C=CC(=C(C(=O)OCC)C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of ethyl 2-fluoro-5-nitrobenzoate (1.07 g), phenol (565 mg), potassium carbonate (1.38 g) and N,N-dimethylformamide (20 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extrac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Aromatic alcohol | Ether.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CN(C=O)C | 80 | 4 | CCOC(=O)c1cc([N+](=O)[O-])ccc1F.Oc1ccccc1>CN(C=O)C>CCOC(=O)c1cc(N)ccc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef295f3049624ba9a6f932b5d9010853 | CCOC(=O)c1ccc(CBr)cc1.CSc1ncnc2cn[nH]c12>>COC(=O)c1ccc(Cn2cc3ncnc(SC)c3n2)cc1.COC(=O)c1ccc(Cn2ncc3ncnc(SC)c32)cc1 | BrCC1=CC=C(C(=O)OCC)C=C1.CSC=1C2=C(N=CN1)C=NN2.[H-].[Na+]>>CSC=1C2=C(N=CN1)C=NN2CC2=CC=C(C(=O)OC)C=C2.CSC=1C=2C(N=CN1)=CN(N2)CC2=CC=C(C(=O)OC)C=C2 | Br[CH2:31][c:30]1[cH:29][cH:28][c:5]([C:3]([O:2][CH2:1][CH3:35])=[O:4])[cH:44][cH:43]1.[n:10]1[cH:11][c:12]2[n:13][cH:14][n:15][c:16]([S:17][CH3:18])[c:19]2[nH:32]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][c:12]3[n:13][cH:14][n:15][c:16]([S:17][CH3:18])[c:19]3[n:20]2)[cH:21][cH:22]1.[CH3:... | CCOC(=O)c1ccc(CBr)cc1.CSc1ncnc2cn[nH]c12 | COC(=O)c1ccc(Cn2cc3ncnc(SC)c3n2)cc1.COC(=O)c1ccc(Cn2ncc3ncnc(SC)c32)cc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 69f8b9b6349b792a0dee6d904c29ee7cfdff387e4eb2eb980499c901083fef5f | 08b2a64655eebd58f53d97b92771b7d831c3b6cc8b1b6b6d538729fc2ee365d7 | c1ccc(Cn2cc3ncncc3n2)cc1.c1ccc(Cn2ncc3ncncc32)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10]):[cH;D2;+0:11]:[c:12]:1.[#16:13]-[c:14]1:[#7;a:15]:[c:16]:[#7;a:17]:[c:18]2:[c:19]:[n;H0;D2;+0:20]:[nH;D2;+0:21]:[c;H0;D3;+0:22]:2:1>>[#16:13]-[c:14]1:[#7;a:15]:[c:16]:[#7;a:17]:[c:18]2:[c:19]:[n;H0;D3;+0:... | null | [] | null | null | 10 | MINUTE | To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (400 mg) in N,N-dimethylformamide (8 mL) was added 60% sodium hydride (98 mg) under ice-cooling, and the mixture was stirred at room temperature for 10 min. Then, ethyl 4-(bromomethyl)benzoate (606 mg) was added under ice-cooling, and the mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ester.Monosulfide | c1ccccc1.c1ncc2n[nH]cc2n1 | c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1.c1ncnc2cn[nH]c12 | c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1.c1ncnc2cn[nH]c12 | Br- | CN(C=O)C.C(C)(=O)OCC | null | 0.166667 | CCOC(=O)c1ccc(CBr)cc1.CSc1ncnc2cn[nH]c12>CN(C=O)C.C(C)(=O)OCC>COC(=O)c1ccc(Cn2cc3ncnc(SC)c3n2)cc1.COC(=O)c1ccc(Cn2ncc3ncnc(SC)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86ec5f319157400a82c7853df2ab732b | CSc1ncnc2cn[nH]c12.O=C(OCCI)c1ccccc1.O=C([O-])[O-]>>CSc1ncnc2cn(CCOC(=O)c3ccccc3)nc12.CSc1ncnc2cnn(CCOC(=O)c3ccccc3)c12 | O.CSC=1C2=C(N=CN1)C=NN2.C(C1=CC=CC=C1)(=O)OCCI.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)(=O)OCCN1N=CC=2N=CN=C(C21)SC.C(C1=CC=CC=C1)(=O)OCCN1N=C2C(N=CN=C2SC)=C1 | [CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[c:22]1[nH:9][n:31][cH:30]2.I[CH2:33][CH2:34][O:35][C:36](=[O:37])[c:38]1[cH:39][cH:8][cH:41][cH:42][cH:43]1.[O-][C:13]([O-:12])=[O:14]>>[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9]([CH2:10][CH2:11][O:12][C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21][c:2... | CSc1ncnc2cn[nH]c12.O=C(OCCI)c1ccccc1.O=C([O-])[O-] | CSc1ncnc2cn(CCOC(=O)c3ccccc3)nc12.CSc1ncnc2cnn(CCOC(=O)c3ccccc3)c12 | null | null | CN(C=O)C.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 2bb4372b727939bd66414920f948f4a18409fc06951c5403c00c20d9203b9606 | 9259a53dabfdb3b1d2386fadb2d5599dab233d24a6464e15b3982bff7ce113b5 | O=C(OCCn1cc2ncncc2n1)c1ccccc1.O=C(OCCn1ncc2ncncc21)c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1.[#16:12]-[c:13]1:[#7;a:14]:[c:15]:[#7;a:16]:[c;H0;D3;+0:17]2:[cH;D2;+0:18]:[n;H0;D2;+0:19]:[nH;D2;+0:20]:[c;H0;D3;+0:21]:1:2.[O-;H0;D1:22]-[C;H0;D3;+0:23](-[O-])=[O;D1;H0:24]>>[#16:12]-[c:13]1:[#7;a:14]:[c:15]... | null | [] | 60 | CELSIUS | 1 | HOUR | To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (300 mg) and 2-iodoethyl benzoate (548 mg) in N,N-dimethylformamide (10 mL) was added potassium carbonate (374 mg), and the mixture was stirred at 60° C. for 1 hr. After the completion of the reaction, water was added to the reaction mixture. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester.Monosulfide | c1ncc2[nH]ncc2n1.c1ccccc1 | c1ncnc2c[nH]nc12.c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1 | c1ncnc2c[nH]nc12.c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1 | I- | CN(C=O)C.C(C)(=O)OCC | 60 | 1 | CSc1ncnc2cn[nH]c12.O=C(OCCI)c1ccccc1.O=C([O-])[O-]>CN(C=O)C.C(C)(=O)OCC>CSc1ncnc2cn(CCOC(=O)c3ccccc3)nc12.CSc1ncnc2cnn(CCOC(=O)c3ccccc3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05c9281cf7174921872b575bc7b9f531 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Cl.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1 | ClC=1C2=C(N=CN1)C=CN2.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2 | [Cl:1][c:15]1[n:16][cH:17][n:18][c:19]2[cH:20][cH:21][nH:22][c:23]12.[F:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:24][c:25]2[Cl:26])[cH:27]1>>[ClH:1].[F:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][n:18][c:19]4[cH:20][cH:2... | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Cl.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1 | null | null | CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[ClH;D0;+0:1].[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1):[c:14] | 79.7 | [{"value": 79.7, "product": "Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (770 mg) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (2.52 g) were dissolved in 1-methyl-2-pyrrolidone (10 mL), and the mixture was stirred with heating at 140° C. for 2.5 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (300 mL), and stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1 | null | CN1C(CCC1)=O.C(C)(=O)OCC | 140 | null | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O.C(C)(=O)OCC>Cl.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db16c6dc72874539acf910e6e61b0c11 | Clc1ncnc2cc[nH]c12.OCc1ccc(CCl)cc1>>OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].OCC1=CC=C(CCl)C=C1>>ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)CO | [nH:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]12.Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:19][cH:18]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]23)[cH:18][cH:19]1 | Clc1ncnc2cc[nH]c12.OCc1ccc(CCl)cc1 | OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ncncc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:1>>[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:14]:2:1 | 70 | [{"value": 70.0, "product": "ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (304 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Hydroxymethylbenzyl chloride (377 mg) was added, and the mixture was stirred at room temperature for 16 hrs. After diluting w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12 | HCl | O.CN(C=O)C | null | 0.5 | Clc1ncnc2cc[nH]c12.OCc1ccc(CCl)cc1>O.CN(C=O)C>OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f9d637c337140aeb493704722b3ec7d | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1>>OCc1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)CO.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)CO | [NH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]2)[c:30]([Cl:31])[cH:32]1.Cl[c:15]1[n:14][cH:13][n:12][c:11]2[cH:10][cH:9][n:8]([CH2:7][c:6]3[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:35][cH:34]3)[c:33]21>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][cH:10][c:11]3... | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1 | OCc1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | null | null | CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccccc5)c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 93 | [{"value": 93.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | {4-[(4-Chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanol (354 mg) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (488 mg) were dissolved in 1-methyl-2-pyrrolidone (2.58 mL), and the mixture was stirred with heating at 140° C. for 2 hrs. After cooling to room temperature, the reaction mixture was diluted with e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | CN1C(CCC1)=O.C(C)(=O)OCC | 140 | null | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCc1ccc(Cn2ccc3ncnc(Cl)c32)cc1>CN1C(CCC1)=O.C(C)(=O)OCC>OCc1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5c0dd2c63a3498bb2f7c23fcfcac790 | COc1ccc(C(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1>>COc1ccc(C(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC | Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].COC=1C=C(C(=O)Cl)C=CC1OC>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2C(C2=CC(=C(C=C2)OC)OC)=O | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35]1)=[O:8].[nH:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]4[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]4)[c:31]([Cl:32])[cH:33]3)[c:34]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])... | COc1ccc(C(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1 | COc1ccc(C(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC | null | null | CN(C=O)C | Acylation | N-alkylation of secondary amines with alkyl halides | 9634436895a68d22c17052eb8c6668ee472dd157e0a2b08481637c8cdacda3d9 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(c1ccccc1)n1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[nH;D2;+0:14]:[c:15]:2:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[n;H0;D3;+0:14](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:15]:2:1 | 52.7 | [{"value": 52.7, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2C(C2=CC(=C(C=C2)OC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, to a suspension of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride (150 mg) and potassium carbonate (102 mg) in N,N-dimethylformamide (1.5 mL) was added 3,4-dimethoxybenzoyl chloride (82 mg), and the mixture was stirred under ice-cooling, for 1 hr. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | null | COc1ccc(C(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1>CN(C=O)C>COc1ccc(C(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a0c8916f36844eab3c72dcde4c1fc95 | COC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)OC)C=C2.Cl>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)O)C=C2 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]23)[cH:35][cH:36]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:... | COC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | null | null | O1CCCC1.O.[OH-].[Na+].C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccccc5)c34)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 89.2 | [{"value": 89.2, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Methyl 4-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoate (850 mg) was dissolved in a mixed solvent of ethanol (3.29 mL)/tetrahydrofuran (3.29 mL), 1N aqueous sodium hydroxide solution (3.29 mL) was added, and the mixture was stirred at room temperature for 20 hrs. 1N ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | O1CCCC1.O.[OH-].[Na+].C(C)O | null | 20 | COC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>O1CCCC1.O.[OH-].[Na+].C(C)O>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfe79ba3cb824953b3c05068c2172966 | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1.OC1CCNCC1>>O=C(c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1)N1CCC(O)CC1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)O)C=C2.OC1CCNCC1.O.ON1N=NC2=C1C=CC=C2.Cl.C(C)N=C=NCCCN(C)C>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)N1CCC(CC1)O)C=C2 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]5[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]5)[c:30]([Cl:31])[cH:32]4)[c:33]23)[cH:34][cH:35]1.[NH:36]1[CH2:37][CH2:38][CH:39]([OH:40])[CH2:41][CH2:42]1>>[O:1]=[C:2]([c:... | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1.OC1CCNCC1 | O=C(c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1)N1CCC(O)CC1 | null | null | C(C)N(CC)CC.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c32)cc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | 96.1 | [{"value": 96.1, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)N1CCC(CC1)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 4-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoic acid (150 mg), 4-hydroxypiperidine (33.2 mg) and 1-hydroxybenzotriazole monohydrate (60 mg) in N,N-dimethylformamide (3 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg) ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HO- | C(C)N(CC)CC.CN(C=O)C | null | 8 | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1.OC1CCNCC1>C(C)N(CC)CC.CN(C=O)C>O=C(c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1)N1CCC(O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d85f0c7f3e0e46c785ab92c76a8cebc7 | Cc1ccc(Oc2ccc(N)cc2C)cn1.O=[N+]([O-])c1c(Cl)ncnc1Cl>>Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1.Cl | ClC1=NC=NC(=C1[N+](=O)[O-])Cl.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C>>Cl.ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:22][c:23]2[CH3:24])[cH:25][n:26]1.[c:12]1([Cl:27])[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]3[N+:19](=[O:20... | Cc1ccc(Oc2ccc(N)cc2C)cn1.O=[N+]([O-])c1c(Cl)ncnc1Cl | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1.Cl | null | null | CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ccncn3)cc2)c1 | [#7;+:1]-[c:2]1:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[Cl;H0;D1;+0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;+:1]-[c:2]1:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13].[ClH;D0;+0:9] | 72 | [{"value": 72.0, "product": "Cl.ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 1 | HOUR | 4,6-Dichloro-5-nitropyrimidine (9.7 g) was dissolved in 1-methyl-2-pyrrolidone (25.7 mL), a solution of 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (5.35 g) in 1-methyl-2-pyrrolidone (10 mL) was added dropwise under cooling at −15° C., and the mixture was stirred at −10° C. to 0° C. for 1 hr. The mixture was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1 | null | CN1C(CCC1)=O.C(C)(=O)OCC | -15 | 1 | Cc1ccc(Oc2ccc(N)cc2C)cn1.O=[N+]([O-])c1c(Cl)ncnc1Cl>CN1C(CCC1)=O.C(C)(=O)OCC>Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e7acefcc0d942839d9faaf8e8293dc5 | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1 | [OH-].[Na+].O.O.[Sn](Cl)(Cl)(Cl)Cl.Cl.ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)[N+](=O)[O-].C(C)(=O)OCC>>ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N | O=[N+:19]([O-])[c:18]1[c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:24][cH:23]3)[c:21]([CH3:22])[cH:20]2)[n:13][cH:14][n:15][c:16]1[Cl:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]3[NH2:19])[cH:20][c:21]2[CH3:22]... | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1 | null | null | Cl.C(C)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cncc(Oc2ccc(Nc3ccncn3)cc2)c1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:2]:1-[NH2;D1;+0:1] | 76.1 | [{"value": 76.1, "product": "ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 6-Chloro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5-nitropyrimidin-4-amine hydrochloride (2.04 g) was suspended in diethyl ether (9.45 mL) and a solution of tin(IV) chloride dihydrate (9.1 g) in conc. hydrochloric acid (20.17 mL) was added under ice-cooling. After stirring at room temperature for 3 hrs, the rea... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1.c1cncnc1 | Other | Cl.C(C)OCC | null | 3 | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3[N+](=O)[O-])cc2C)cn1>Cl.C(C)OCC>Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4226dfb0ba9b476a983799e165bc9e57 | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1.[I-]>>Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1.I | C(O)([O-])=O.[Na+].ClC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.[I-].[Na+].O>>I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N | Cl[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:24][cH:23]3)[c:21]([CH3:22])[cH:20]2)[c:18]1[NH2:19].[I-:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]([I:17])[c:18]3[NH2:19])[cH:20][c:21]2[CH3:22])[cH:... | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1.[I-] | Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1.I | null | null | I.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 0e5e018dae2d5b301dea7fbf3d4d324b1e81c774be63c615b15b41b2296e4e71 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1cncc(Oc2ccc(Nc3ccncn3)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[I-;H0;D0:9]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[I;H0;D1;+0:9]):[c:7]:1-[N;D1;H2:8] | 95.3 | [{"value": 95.3, "product": "I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | 6-Chloro-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine (400 mg) was suspended in 55% hydriodic acid (6.16 mL), sodium iodide (878 mg) was added, and the mixture was stirred with heating at 70° C. for 10 min. After cooling to room temperature, water (40 mL)/ethyl acetate (30 mL) was added. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1 | null | I.C(C)(=O)OCC | 70 | null | Cc1ccc(Oc2ccc(Nc3ncnc(Cl)c3N)cc2C)cn1.[I-]>I.C(C)(=O)OCC>Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1.I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31e1da1d74164f3a9392798a95736361 | CC#N.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(N)c4)c3N)cc2C)cn1 | I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.C(C)#N>>NC=1C=C(C=CC1)C#CC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N | [C:17]([CH3:21])#[N:24].I[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:32][cH:31]3)[c:29]([CH3:30])[cH:28]2)[c:26]1[NH2:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]([C:17]#[C:18][c:19]4[cH:20][cH:21][... | CC#N.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(N)c4)c3N)cc2C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)N(CC)CC.C(#C)C=1C=C(N)C=CC1 | Aromatic Heterocycle Formation | OtherReaction | 9479db21649e30fa62ec6536b7f69bbd536b5b3c68b5c30e0fb864e7cf23f38c | ecdc94851be19e19a274edc6d2f8ac2fade83b0d0869127678215e856fcafd6f | C(#Cc1cc(Nc2ccc(Oc3cccnc3)cc2)ncn1)c1ccccc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[CH3;D1;+0:9]-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:10]#[C:12]-[c:13]2:[c:14]:[cH;D2;+0:9]:[c:15]:[c:16](-[NH2;D1;+0:11]):[c:17]:2):[c:7]:1-[N;D1;H2:8] | null | [] | null | null | 1.5 | HOUR | 6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (200 mg) was dissolved in a mixed solvent of acetonitrile (7.6 mL)/triethylamine (5.72 mL), 3-ethynylaniline (0.0574 mL), trans-dichlorobis(triphenylphosphine)palladium(II) (15.4 mg) and copper(I) iodide (5.3 mg) were sequentiall... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrile | Primary amine.Alkyne | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccncc1.c1ccccc1.c1cncnc1.c1ccccc1 | I- | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)N(CC)CC.C(#C)C=1C=C(N)C=CC1 | null | 1.5 | CC#N.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)N(CC)CC.C(#C)C=1C=C(N)C=CC1>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(N)c4)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ab1f8bae8a043e4b9fa9fee77ad79a2 | C#Cc1ccc(N)cc1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4ccc(N)cc4)c3N)cc2C)cn1 | I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.C(#C)C1=CC=C(N)C=C1>>NC1=CC=C(C=C1)C#CC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N | [CH:17]#[C:18][c:19]1[cH:20][cH:21][c:22]([NH2:23])[cH:24][cH:25]1.I[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:32][cH:31]3)[c:29]([CH3:30])[cH:28]2)[c:26]1[NH2:27]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15... | C#Cc1ccc(N)cc1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4ccc(N)cc4)c3N)cc2C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cc(Nc2ccc(Oc3cccnc3)cc2)ncn1)c1ccccc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[CH;D1;+0:9]#[C:10]-[c:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:10]-[c:11]):[c:7]:1-[N;D1;H2:8] | 65.9 | [{"value": 65.9, "product": "NC1=CC=C(C=C1)C#CC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (270 mg) was dissolved in a mixed solvent of acetonitrile (10.3 mL)/triethylamine (7.72 mL), and 4-ethynylaniline (80.3 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (20.8 mg) and copper(I) iodide (7.16 mg) were sequent... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#Cc1ccc(N)cc1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4ccc(N)cc4)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b9adc720be54eb48d919d4ef7b1d0db | COCC(=O)O.Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(N)cc5)[nH]c34)cc2C)cn1>>COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(Oc5ccc(C)nc5)c(C)c4)c3[nH]2)cc1 | Cl.C(C)N=C=NCCCN(C)C.NC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C.COCC(=O)O.O.ON1N=NC2=C1C=CC=C2>>COCC(=O)NC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C | O[C:4]([CH2:3][O:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][c:24]5[cH:25][cH:26][c:27]([CH3:28])[n:29][cH:30]5)[c:31]([CH3:32])[cH:33]4)[c:34]3[nH:35]2)[cH:36][cH:37]1>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9... | COCC(=O)O.Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(N)cc5)[nH]c34)cc2C)cn1 | COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(Oc5ccc(C)nc5)c(C)c4)c3[nH]2)cc1 | null | null | ClCCl.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2cc3ncnc(Nc4ccc(Oc5cccnc5)cc4)c3[nH]2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 8 | HOUR | To a mixture of 6-(4-aminophenyl)-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (40 mg), methoxyacetic acid (0.0145 mL) and 1-hydroxybenzotriazole monohydrate (38 mg) in N,N-dimethylformamide (1.9 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54 mg) an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1.c1ccncc1 | HO- | ClCCl.C(C)N(CC)CC.CN(C=O)C | null | 8 | COCC(=O)O.Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(N)cc5)[nH]c34)cc2C)cn1>ClCCl.C(C)N(CC)CC.CN(C=O)C>COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(Oc5ccc(C)nc5)c(C)c4)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c26f329438144e5a573a4dafd81a192 | CCOC(=O)c1[nH]c(-c2ccc(OC)cc2)cc1N.N=CN>>COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1 | NC1=C(NC(=C1)C1=CC=C(C=C1)OC)C(=O)OCC.C(=N)N>>COC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)O | CCO[C:13](=[O:14])[c:15]1[c:9]([NH2:10])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[nH:16]1.N[CH:11]=[NH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[n:10][cH:11][n:12][c:13]([OH:14])[c:15]3[nH:16]2)[cH:17][cH:18]1 | CCOC(=O)c1[nH]c(-c2ccc(OC)cc2)cc1N.N=CN | COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1 | null | null | O1CCCC1.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 18676698bc1e56bd5ff1be71d10b0382d6f0e2c88c191655a5947d8927e09a11 | be53a05fe81ad29ab5edbac9868dcfdb06310f53b9ff1c00e98e247b0cca57da | c1ccc(-c2cc3ncncc3[nH]2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[NH2;D1;+0:8].N-[CH;D2;+0:9]=[NH;D1;+0:10]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[c:7]2:[c:6]:[c:5]:[#7;a:4]:[c:3]:2:1 | 11.5 | [{"value": 11.5, "product": "COC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 16 | HOUR | Ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (7.2 g) was dissolved in tetrahydrofuran (16 mL)/ethanol (32 mL), formamidine (3.46 g) was added, and the mixture was stirred at 90° C. for 16 hrs. After cooling to room temperature, tetrahydrofuran was evaporated under reduced pressure. The residue was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | Aromatic alcohol | c1cc[nH]c1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1 | HO- | O1CCCC1.C(C)O | 90 | 16 | CCOC(=O)c1[nH]c(-c2ccc(OC)cc2)cc1N.N=CN>O1CCCC1.C(C)O>COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e43e5db6e580456d9a4f69a348f2ca38 | COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl>>COc1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1 | COC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)O.N.P(=O)(Cl)(Cl)Cl.ClCCCl>>ClC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C=C2)OC | O[c:13]1[n:12][cH:11][n:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]3)[nH:16][c:15]21.O=P(Cl)(Cl)[Cl:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]3[nH:16]2)[cH:17][cH:18]1 | COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl | COc1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1 | null | null | O1CCCC1.C(C)N(C1=CC=CC=C1)CC | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 2abe710ccd285a9ab92e9161186a087fb3ea26b59ffc48b8e24881a6657aca35 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cc3ncncc3[nH]2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1 | null | [] | 110 | CELSIUS | null | null | 6-(4-Methoxyphenyl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol (500 mg) was suspended in N,N-diethylaniline (1.11 mL)/1,2-dichloroethane (3.73 mL), phosphorus oxychloride (2.29 mL) was added, and the mixture was stirred with heating at 110° C. for 2 hrs. After cooling to room temperature, the reaction mixture was treated with ice... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1 | HCl | O1CCCC1.C(C)N(C1=CC=CC=C1)CC | 110 | null | COc1ccc(-c2cc3ncnc(O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl>O1CCCC1.C(C)N(C1=CC=CC=C1)CC>COc1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae0ffbc24bf94abf8f27c817017de8b9 | C#Cc1cccc(CNC(=O)OC(C)(C)C)c1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(CNC(=O)OC(C)(C)C)c4)c3N)cc2C)cn1 | I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.C(#C)C=1C=C(CNC(OC(C)(C)C)=O)C=CC1>>NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#CC=1C=C(CNC(OC(C)(C)C)=O)C=CC1 | [CH:17]#[C:18][c:19]1[cH:20][cH:21][cH:22][c:23]([CH2:24][NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33]1.I[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:40][cH:39]3)[c:37]([CH3:38])[cH:36]2)[c:34]1[NH2:35]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](... | C#Cc1cccc(CNC(=O)OC(C)(C)C)c1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(CNC(=O)OC(C)(C)C)c4)c3N)cc2C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cc(Nc2ccc(Oc3cccnc3)cc2)ncn1)c1ccccc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[CH;D1;+0:9]#[C:10]-[c:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:10]-[c:11]):[c:7]:1-[N;D1;H2:8] | 78.6 | [{"value": 78.6, "product": "NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#CC=1C=C(CNC(OC(C)(C)C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (500 mg) was dissolved in a mixed solvent of acetonitrile (14.8 mL)/triethylamine (11.0 mL), and tert-butyl 3-ethynylbenzylcarbamate (247 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (31.3 mg) and copper(I) iodide (10.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#Cc1cccc(CNC(=O)OC(C)(C)C)c1.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Cc1ccc(Oc2ccc(Nc3ncnc(C#Cc4cccc(CNC(=O)OC(C)(C)C)c4)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c17533672144538af8d2d4610f9827a | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CNC(=O)OC(C)(C)C)c5)[nH]c34)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CN)c5)[nH]c34)cc2C)cn1 | CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C=2C=C(CNC(OC(C)(C)C)=O)C=CC2.Cl.[OH-].[Na+]>>NCC=1C=C(C=CC1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C | CC(C)(C)OC(=O)[NH:25][CH2:24][c:23]1[cH:22][cH:21][cH:20][c:19](-[c:18]2[cH:17][c:16]3[n:15][cH:14][n:13][c:12]([NH:11][c:10]4[cH:9][cH:8][c:7]([O:6][c:5]5[cH:4][cH:3][c:2]([CH3:1])[n:33][cH:32]5)[c:30]([CH3:31])[cH:29]4)[c:28]3[nH:27]2)[cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12... | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CNC(=O)OC(C)(C)C)c5)[nH]c34)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CN)c5)[nH]c34)cc2C)cn1 | null | null | O1CCCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cc3ncnc(Nc4ccc(Oc5cccnc5)cc4)c3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 87.7 | [{"value": 87.7, "product": "NCC=1C=C(C=CC1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | tert-Butyl 3-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzylcarbamate (230 mg) was suspended in tetrahydrofuran (2.3 mL), 2N hydrochloric acid (2.3 mL) was added, and the mixture was stirred with heating at 60° C. for 3 hrs. After cooling to room temperature, 1N aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HO- | O1CCCC1 | 60 | null | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CNC(=O)OC(C)(C)C)c5)[nH]c34)cc2C)cn1>O1CCCC1>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5cccc(CN)c5)[nH]c34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad29a69ef23740bf8672496c4623d8d1 | C#CCNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(C#CCNC(=O)OC(C)(C)C)c3N)cc2C)cn1 | I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.C(C#C)NC(OC(C)(C)C)=O>>NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#CCNC(OC(C)(C)C)=O | [CH:17]#[C:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].I[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:34][cH:33]3)[c:31]([CH3:32])[cH:30]2)[c:28]1[NH2:29]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3... | C#CCNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(C#CCNC(=O)OC(C)(C)C)c3N)cc2C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cncc(Oc2ccc(Nc3ccncn3)cc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[C:9]-[C:10]#[CH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:11]#[C:10]-[C:9]):[c:7]:1-[N;D1;H2:8] | 73.8 | [{"value": 73.8, "product": "NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (500 mg) was dissolved in a mixed solvent of acetonitrile (14.8 mL)/triethylamine (11.0 mL), and tert-butyl 2-propynylcarbamate (166 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (31.3 mg) and copper(I) iodide (10.2 mg)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#CCNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Cc1ccc(Oc2ccc(Nc3ncnc(C#CCNC(=O)OC(C)(C)C)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8076fb2b785b432da01a6555b29f9f2b | C#C/C=C/CNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc(C#C/C=C/CNC(=O)OC(C)(C)C)c3N)cc2C)cn1 | I.IC1=C(C(=NC=N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)N.C(\C=C\C#C)NC(OC(C)(C)C)=O>>NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#C/C=C/CNC(OC(C)(C)C)=O | [CH:17]#[C:18]/[CH:19]=[CH:20]/[CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29].I[c:16]1[n:15][cH:14][n:13][c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([O:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[n:36][cH:35]3)[c:33]([CH3:34])[cH:32]2)[c:30]1[NH2:31]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:1... | C#C/C=C/CNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc(C#C/C=C/CNC(=O)OC(C)(C)C)c3N)cc2C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cncc(Oc2ccc(Nc3ccncn3)cc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[C:9]/[C:10]=[C:11]/[C:12]#[CH;D1;+0:13]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:13]#[C:12]/[C:11]=[C:10]/[C:9]):[c:7]:1-[N;D1;H2:8] | 45.9 | [{"value": 45.9, "product": "NC=1C(=NC=NC1NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C)C#C/C=C/CNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (500 mg) was dissolved in a mixed solvent of acetonitrile (14.8 mL)/triethylamine (11.0 mL), and tert-butyl (2E)-2-penten-4-yn-1-ylcarbamate (194 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (31.3 mg) and copper(I) iod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1ccncc1.c1ccccc1.c1cncnc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#C/C=C/CNC(=O)OC(C)(C)C.Cc1ccc(Oc2ccc(Nc3ncnc(I)c3N)cc2C)cn1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Cc1ccc(Oc2ccc(Nc3ncnc(C#C/C=C/CNC(=O)OC(C)(C)C)c3N)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ded10e89a71c4d389ae0f9a7b910f953 | Nc1c(I)ncnc1I.Oc1ccccc1>>Nc1c(I)ncnc1Oc1ccccc1 | IC1=NC=NC(=C1N)I.C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+]>>IC1=NC=NC(=C1N)OC1=CC=CC=C1 | I[c:8]1[c:2]([NH2:1])[c:3]([I:4])[n:5][cH:6][n:7]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[NH2:1][c:2]1[c:3]([I:4])[n:5][cH:6][n:7][c:8]1[O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | Nc1c(I)ncnc1I.Oc1ccccc1 | Nc1c(I)ncnc1Oc1ccccc1 | null | null | CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[I;D1;H0:6]):[c:7]:1-[N;D1;H2:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[I;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1-[N;D1;H2:8] | 100.7 | [{"value": 100.7, "product": "IC1=NC=NC(=C1N)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 16 | HOUR | 4,6-Diiodopyrimidin-5-amine (2.2 g) was dissolved in 1-methyl-2-pyrrolidone (11.5 mL), phenol (656 mg) and potassium carbonate (964 mg) were added, and the mixture was stirred at 100° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 mL) and washed successively with water... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | CN1C(CCC1)=O.C(C)(=O)OCC | 100 | 16 | Nc1c(I)ncnc1I.Oc1ccccc1>CN1C(CCC1)=O.C(C)(=O)OCC>Nc1c(I)ncnc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccbcaae9a5f940c3a8350c0dd2d6f435 | C#C/C=C/CO[Si](C)(C)C(C)(C)C.Nc1c(I)ncnc1Oc1ccccc1>>CC(C)(C)[Si](C)(C)OC/C=C/C#Cc1ncnc(Oc2ccccc2)c1N | IC1=NC=NC(=C1N)OC1=CC=CC=C1.C(C)(C)(C)[Si](OC\C=C\C#C)(C)C>>[Si](C)(C)(C(C)(C)C)OC/C=C/C#CC1=NC=NC(=C1N)OC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]#[CH:13].I[c:14]1[n:15][cH:16][n:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]1[NH2:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]#[C:13][c:14]1[n:15][cH:16][n:17... | C#C/C=C/CO[Si](C)(C)C(C)(C)C.Nc1c(I)ncnc1Oc1ccccc1 | CC(C)(C)[Si](C)(C)OC/C=C/C#Cc1ncnc(Oc2ccccc2)c1N | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Oc2ccncn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[N;D1;H2:8].[C:9]/[C:10]=[C:11]/[C:12]#[CH;D1;+0:13]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:13]#[C:12]/[C:11]=[C:10]/[C:9]):[c:7]:1-[N;D1;H2:8] | 87.8 | [{"value": 87.8, "product": "[Si](C)(C)(C(C)(C)C)OC/C=C/C#CC1=NC=NC(=C1N)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Iodo-6-phenoxypyrimidin-5-amine (1.0 g) was dissolved in a mixed solvent of acetonitrile (53 mL)/triethylamine (39 mL), and tert-butyl(dimethyl)[(2E)-2-penten-4-ynyloxy]silane (753 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (112 mg) and copper(I) iodide (36.5 mg) were sequentially added. The title compou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#C/C=C/CO[Si](C)(C)C(C)(C)C.Nc1c(I)ncnc1Oc1ccccc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>CC(C)(C)[Si](C)(C)OC/C=C/C#Cc1ncnc(Oc2ccccc2)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad3b6a294f744dfd8cf1500c0e64560d | CC(C)(C)[Si](C)(C)OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1.CCI>>CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21 | [Si](C)(C)(C(C)(C)C)OC/C=C/C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+].ICC>>[Si](C)(C)(C(C)(C)C)OC/C=C/C1=CC=2N=CN=C(C2N1CC)OC1=CC=CC=C1 | [nH:3]1[c:4](/[CH:5]=[CH:6]/[CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]2[n:18][cH:19][n:20][c:21]([O:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:29]12.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][n:3]1[c:4](/[CH:5]=[CH:6]/[CH2:7][O:8][Si:9]([CH3:10])([CH3:11])[C:12]([CH3:13])([CH3:14... | CC(C)(C)[Si](C)(C)OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1.CCI | CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e9fbaa0885668a0db6604d7955d2895802f0f03f498828bb48474e6359c120b7 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10](/[C:11]=[C:12]/[C:13]):[nH;D2;+0:14]:[c:15]:2:1>>[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10](/[C:11]=[C:12]/[C:13]):[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:15]:2:1 | null | [] | null | null | 20 | MINUTE | 6-((1E)-3-{[tert-Butyl(dimethyl)silyl]oxy}-1-propenyl)-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (100 mg) was dissolved in N,N-dimethylformamide (0.786 mL), cesium carbonate (102.6 mg) was added, and the mixture was stirred at room temperature for 20 min. Iodoethane (0.0231 mL) was added and the mixture was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccccc1 | HI | CN(C=O)C.C(C)(=O)OCC | null | 0.333333 | CC(C)(C)[Si](C)(C)OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1.CCI>CN(C=O)C.C(C)(=O)OCC>CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb44393fedd44638a22d225f917392a8 | CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>>CCn1c(/C=C/CO)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | [Si](C)(C)(C(C)(C)C)OC/C=C/C1=CC=2N=CN=C(C2N1CC)OC1=CC=CC=C1.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C.Cl.N1=CC=CC=C1.C1(=CC=CC=C1)O>>C(C)N1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)/C=C/CO | CC(C)(C)[Si](C)(C)[O:8][CH2:7]/[CH:6]=[CH:5]/[c:4]1[n:3]([CH2:2][CH3:1])[c:31]2[c:10]([cH:9]1)[n:11][cH:12][n:13][c:14]2Oc1ccccc1.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][c:24]([CH3:25])[n:26][cH:27]2)[c:28]([CH3:29])[cH:30]1>>[CH3:1][CH2:2][n:3]1[c:4](/[CH:5]=[CH:6]/[CH2:7][OH:8])[cH:9][c:10]2[n... | CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1 | CCn1c(/C=C/CO)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | a1eaf5ebc4b4900f6857056acac1768d131704c45cce2efb15e191262f5f7179 | f5f4bef2dd57edef4ab5c305326a2437314e70311439cfd2555321357dbf7835 | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]/[C:3]=[C:4]/[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11](-O-c3:c:c:c:c:c:3):[c:12]:2:[#7;a:13]:1-[C:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C:14]-[#7;a:13]1:[c:12]2:[c:7](:[#7;a:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11]:2-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]):[... | 40.4 | [{"value": 40.4, "product": "C(C)N1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 6-((1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propenyl)-5-ethyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (78 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (61.2 mg), pyridine hydrochloride (26 mg) and phenol (122 mg) was stirred with heating at 120° C. for 16 hrs. After cooling to room temperature, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.TMS ether protective group | Primary alcohol.Secondary amine | c1cc2ncncc2[nH]1.c1ccccc1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccccc1.c1ccncc1 | HO- | ClCCl | 120 | null | CCn1c(/C=C/CO[Si](C)(C)C(C)(C)C)cc2ncnc(Oc3ccccc3)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>ClCCl>CCn1c(/C=C/CO)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1faed6812f684d00b3aaf60cd35bf7e6 | Nc1c(I)ncnc1Oc1ccccc1>>Nc1c(C#CCO)ncnc1Oc1ccccc1 | IC1=NC=NC(=C1N)OC1=CC=CC=C1>>NC=1C(=NC=NC1OC1=CC=CC=C1)C#CCO | I[c:3]1[c:2]([NH2:1])[c:11]([O:7][c:13]2[cH:4][cH:17][cH:16][cH:15][cH:14]2)[n:10][cH:9][n:8]1>>[NH2:1][c:2]1[c:3]([C:4]#[C:5][CH2:6][OH:7])[n:8][cH:9][n:10][c:11]1[O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Nc1c(I)ncnc1Oc1ccccc1 | Nc1c(C#CCO)ncnc1Oc1ccccc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC.C(C#C)O | Functional Group Interconversion | OtherReaction | 57ebbe5fd5c1741fec67270624e2926453ae7b2f9493e06540b1b522a4865675 | 44d512cffe65b29b4402cc366a02515ed1e944ff9cea2dc70b9806744975fec2 | c1ccc(Oc2ccncn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:2):[c:13]:1-[N;D1;H2:14]>>[N;D1;H2:14]-[c:13]1:[c;H0;D3;+0:5](-[#8:15]-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[c:16]:2):[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:1... | 174.8 | [{"value": 174.8, "product": "NC=1C(=NC=NC1OC1=CC=CC=C1)C#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Iodo-6-phenoxypyrimidin-5-amine (3.0 g) was dissolved in a mixed solvent of acetonitrile (159 mL)/triethylamine (117 mL), and 2-propyn-1-ol (0.669 mL), trans-dichlorobis(triphenylphosphine)palladium(II) (336 mg) and copper(I) iodide (109.5 mg) were sequentially added. The title compound (2.02 g) was obtained as cryst... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Ether.Primary alcohol.Alkyne | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | I- | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC.C(C#C)O | null | null | Nc1c(I)ncnc1Oc1ccccc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC.C(C#C)O>Nc1c(C#CCO)ncnc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1465727f5cd409da766af7fb0f88633 | C#CC=CCO.Nc1c(I)ncnc1Oc1ccccc1>>Nc1c(C#C/C=C/CO)ncnc1Oc1ccccc1 | IC1=NC=NC(=C1N)OC1=CC=CC=C1.C(C=CC#C)O>>NC=1C(=NC=NC1OC1=CC=CC=C1)C#C/C=C/CO | [CH:4]#[C:5][CH:6]=[CH:7][CH2:8][OH:9].I[c:3]1[c:2]([NH2:1])[c:13]([O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:12][cH:11][n:10]1>>[NH2:1][c:2]1[c:3]([C:4]#[C:5]/[CH:6]=[CH:7]/[CH2:8][OH:9])[n:10][cH:11][n:12][c:13]1[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C#CC=CCO.Nc1c(I)ncnc1Oc1ccccc1 | Nc1c(C#C/C=C/CO)ncnc1Oc1ccccc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Oc2ccncn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[N;D1;H2:8].[C:9]-[C:10]=[C:11]-[C:12]#[CH;D1;+0:13]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:13]#[C:12]/[C:11]=[C:10]/[C:9]):[c:7]:1-[N;D1;H2:8] | 59.9 | [{"value": 59.9, "product": "NC=1C(=NC=NC1OC1=CC=CC=C1)C#C/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Iodo-6-phenoxypyrimidin-5-amine (3.5 g) was dissolved in a mixed solvent of acetonitrile (185 mL)/triethylamine (136 mL), and 2-penten-4-yn-1-ol (1.1 g), trans-dichlorobis(triphenylphosphine)palladium(II) (392 mg) and copper(I) iodide (127 mg) were sequentially added. The title compound (1.79 g) was obtained as a pow... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | null | C#CC=CCO.Nc1c(I)ncnc1Oc1ccccc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Nc1c(C#C/C=C/CO)ncnc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-026c3dfd89c6443588b4b5eb3201a1cf | O=C(Cl)c1ccccc1.OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1>>O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 | O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)/C=C/CO.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)OC\C=C\C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1 | Cl[C:2](=[O:1])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[OH:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][c:9]2[n:10][cH:11][n:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[nH:22]1>>[O:1]=[C:2]([O:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][c:9]2[n:10][cH:11][n:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:1... | O=C(Cl)c1ccccc1.OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1 | O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]/[C:8]=[C:9]/[C:10]-[OH;D1;+0:11]>>[#7;a:6]:[c:7]/[C:8]=[C:9]/[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | (2E)-3-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propen-1-ol (1.0 g) was suspended in tetrahydrofuran (20 mL), and triethylamine (0.651 mL) and benzoyl chloride (0.86 mL) were sequentially added under ice-cooling. The mixture was stirred under ice-cooling for 2 hrs, diluted with ethyl acetate (200 mL) and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | null | O=C(Cl)c1ccccc1.OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1>O1CCCC1.C(C)(=O)OCC>O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c63d315ef4ab4bcd8927f3798919df88 | CI.O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1>>Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21 | O.C([O-])([O-])=O.[K+].[K+].IC.C(C1=CC=CC=C1)(=O)OC\C=C\C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)OC\C=C\C1=CC=2N=CN=C(C2N1C)OC1=CC=CC=C1 | I[CH3:1].[nH:2]1[c:3](/[CH:4]=[CH:5]/[CH2:6][O:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:17]2[n:18][cH:19][n:20][c:21]([O:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:29]12>>[CH3:1][n:2]1[c:3](/[CH:4]=[CH:5]/[CH2:6][O:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:1... | CI.O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 | Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 984dc1e2f23276e16434cf60f0728fced0721ac085a767b5a5daa33828d25b2d | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1 | I-[CH3;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9](/[C:10]=[C:11]/[C:12]):[nH;D2;+0:13]:[c:14]:2:1>>[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9](/[C:10]=[C:11]/[C:12]):[n;H0;D3;+0:13](-[CH3;D1;+0:1]):[c:14]:2:1 | 58 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)(=O)OC\\C=C\\C1=CC=2N=CN=C(C2N1C)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | (2E)-3-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propenyl benzoate (500 mg) was dissolved in N,N-dimethylformamide (4 mL), and potassium carbonate (279 mg) and iodomethane (0.1 mL) were sequentially added. After stirring at room temperature for 4 hrs, water (30 mL) was added to the reaction mixture and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2[nH]ccc2n1 | c1cc2ncncc2[nH]1 | c1ccccc1.c1cc2ncncc2[nH]1.c1ccccc1 | HI | CN(C=O)C | null | 4 | CI.O=C(OC/C=C/c1cc2ncnc(Oc3ccccc3)c2[nH]1)c1ccccc1>CN(C=O)C>Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eeec170076bf4b1ca4a54008ee18cd62 | Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Cn1c(/C=C/CO)cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)(=O)OC\C=C\C1=CC=2N=CN=C(C2N1C)OC1=CC=CC=C1.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.Cl.N1=CC=CC=C1>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2C)/C=C/CO | O=C(c1ccccc1)[O:7][CH2:6]/[CH:5]=[CH:4]/[c:3]1[n:2]([CH3:1])[c:31]2[c:9]([cH:8]1)[n:10][cH:11][n:12][c:13]2Oc1ccccc1.[NH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([F:26])[cH:27]2)[c:28]([Cl:29])[cH:30]1>>[CH3:1][n:2]1[c:3](/[CH:4]=[CH:5]/[CH2:6][OH:7])[cH:8][c:9]2[n:10][cH:11][n:1... | Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Cn1c(/C=C/CO)cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 9f6cea6349504a91cdc9768f306167e35ded894249acbabf53cef7dbb2dc035d | c0530de767090fee49882d17b28eb70d542ad27db18bea6a2b0fe04643a324d6 | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O=C(-[O;H0;D2;+0:1]-[C:2]/[C:3]=[C:4]/[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11](-O-c3:c:c:c:c:c:3):[c:12]:2:[#7;a:13]:1-[C;D1;H3:14])-c1:c:c:c:c:c:1.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:14]-[#7;a:13]1:[c:12]2:[c:7](:[#7;a:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11]:2-[NH;D2;+0:15]-[c:16](:[c:17]):[... | 39.5 | [{"value": 39.5, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2C)/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of (2E)-3-(5-methyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propenyl benzoate (100 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (130 mg), pyridine hydrochloride (36 mg) and 1-methyl-2-pyrrolidone (0.518 mL) was stirred with heating at 140° C. for 4 hrs. After cooling to room temperature, aqueous sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Primary alcohol.Secondary amine | c1ccccc1.c1cc2ncncc2[nH]1.c1ccccc1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccccc1.c1ccccc1 | HO- | CN1C(CCC1)=O | 140 | null | Cn1c(/C=C/COC(=O)c2ccccc2)cc2ncnc(Oc3ccccc3)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O>Cn1c(/C=C/CO)cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-381c2a8b9ebc472ebe4185d0e3002404 | COc1ccc(S(=O)(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1>>COc1ccc(S(=O)(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC | Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].COC=1C=C(C=CC1OC)S(=O)(=O)Cl>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2S(=O)(=O)C2=CC(=C(C=C2)OC)OC | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:37]([O:38][CH3:39])[cH:36]1)(=[O:8])=[O:9].[nH:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]4[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7... | COc1ccc(S(=O)(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1 | COc1ccc(S(=O)(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | f39da367e5fdb20ca9cc942039331e6a114631a43c775eca773ad2c497773002 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1ccccc1)n1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:2:1>>[#7:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:13]:[c:14]:[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:16]:2:1 | 45.1 | [{"value": 45.1, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2S(=O)(=O)C2=CC(=C(C=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride (150 mg) was dissolved in N,N-dimethylformamide (1.5 mL), and potassium carbonate (102 mg) and (3,4-dimethoxyphenyl)sulfonyl chloride (96.9 mg) were sequentially added under ice-cooling. The mixture was stirred under ice-cooling... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 1 | COc1ccc(S(=O)(=O)Cl)cc1OC.Fc1cccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2Cl)c1>CN(C=O)C.C(C)(=O)OCC>COc1ccc(S(=O)(=O)n2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45c2cfdc65294e048ee9111b2f7ed667 | CCOC(=O)c1ccc(CCl)o1.Clc1ncnc2cc[nH]c12>>CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].ClCC1=CC=C(O1)C(=O)OCC>>ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC | Cl[CH2:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:21]1.[nH:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][n:11]2[cH:12][cH:13][c:14]3[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]23)[o:21]1 | CCOC(=O)c1ccc(CCl)o1.Clc1ncnc2cc[nH]c12 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1coc(Cn2ccc3ncncc32)c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[Cl;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[c:15]:[c:16]:[nH;D2;+0:17]:[c:18]:2:1>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[#8;a:4]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:17]1:[c:16]:[c:15]:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10](-[Cl;D1;H0:9]):... | 82.9 | [{"value": 82.9, "product": "ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (500 mg) in N,N-dimethylformamide (6.5 mL) was added potassium carbonate (541 mg) under ice-cooling, and the mixture was stirred for 15 min. while warming to room temperature. Ethyl 5-(chloromethyl)-2-furoate (737 mg) was added to the reaction mixture, and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ccoc1.c1ncnc2cc[nH]c12 | HCl | O.CN(C=O)C | null | 0.25 | CCOC(=O)c1ccc(CCl)o1.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96d72946e7734e8bb4ca9c2e9dc1bbd9 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 | ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:37]3)[c:36]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]2)[c:33]([Cl:34])[cH:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](... | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccco5)c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 90.1 | [{"value": 90.1, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | To a solution of ethyl 5-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate (200 mg) in 1-methyl-2-pyrrolidone (1.3 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (247 mg), and the mixture was heated to 140° C. and stirred for 2 hrs. The reaction mixture was allowed to cool to room temperature, diluted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccoc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 2 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2af15c3b75014d909849c558f42f50fa | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1>>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 | Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC.O1CCCC1.[OH-].[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]23)[o:35]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:11][c:1... | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 | null | null | O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccco5)c34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 67.2 | [{"value": 67.2, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of ethyl 5-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}-2-furoate (280 mg) in a mixed solvent of tetrahydrofuran (1.34 mL) and ethanol (1.34 mL) was added 1N aqueous sodium hydroxide solution (1.34 mL) and the mixture was stirred at room temperature for 14 hr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | O.C(C)O | null | 14 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1>O.C(C)O>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-285c49e9ed884122946d87b7b96a5cf7 | C[C@@H]1CNC[C@H](C)N1.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>>C[C@@H]1CN(C(=O)c2ccc(Cn3ccc4ncnc(Nc5ccc(OCc6cccc(F)c6)c(Cl)c5)c43)cc2)C[C@H](C)N1 | Cl.CN(CCCN=C=NCC)C.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)O)C=C2.C[C@@H]1N[C@@H](CNC1)C.N1(N=NC2=C1C=CC=C2)O>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)C(=O)N2C[C@H](N[C@H](C2)C)C | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:40][C@H:41]([CH3:42])[NH:43]1.O[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([CH2:11][n:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]23)[cH:38][cH:39]1>>[CH3:... | C[C@@H]1CNC[C@H](C)N1.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | C[C@@H]1CN(C(=O)c2ccc(Cn3ccc4ncnc(Nc5ccc(OCc6cccc(F)c6)c(Cl)c5)c43)cc2)C[C@H](C)N1 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 203ddbdbf21b4a3928a7e2e8444b5d8cfa36fbee68b5748d7a1dfab63f3fb59d | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c32)cc1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | 59.5 | [{"value": 59.5, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C=C2)C(=O)N2C[C@H](N[C@H](C2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 4-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoic acid (120 mg) in N,N-dimethylformamide (2.4 mL) were added cis-2,6-dimethylpiperazine (95 mg) and 1H-1,2,3-benzotriazol-1-ol (65 mg), and the mixture was stirred at room temperature for 15 min. N-[3-(Di... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCCN1 | C1CNCC[NH]1 | C1CNCC[NH]1.c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 0.25 | C[C@@H]1CNC[C@H](C)N1.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>O.C(C)N(CC)CC.CN(C=O)C>C[C@@H]1CN(C(=O)c2ccc(Cn3ccc4ncnc(Nc5ccc(OCc6cccc(F)c6)c(Cl)c5)c43)cc2)C[C@H](C)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b64d3bebe9a04930bb2f6c508bd9e7b0 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1>>Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccn1 | ClC=1C2=C(N=CN1)C=CN2.ClC=1C=C(N)C=CC1OCC1=NC=CC=C1>>ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2 | Cl[c:6]1[n:7][cH:8][n:9][c:10]2[cH:11][cH:12][nH:13][c:14]12.[Cl:1][c:2]1[cH:3][c:4]([NH2:5])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][n:25]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][cH:12][nH:13][c:14]23)[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH... | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1 | Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccn1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 77.6 | [{"value": 77.6, "product": "ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (63 mg) in 1-methyl-2-pyrrolidone (0.8 mL), was added 3-chloro-4-(pyridin-2-ylmethoxy)aniline (149 mg), and the mixture was heated to 140° C. and stirred for 2 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccncc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 2 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-731fce796aab4a369b82472af434926b | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2ccccn2)c(Cl)c1>>CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 | ClC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC.ClC=1C=C(N)C=CC1OCC1=NC=CC=C1>>ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:36]3)[c:35]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][n:31]2)[c:32]([Cl:33])[cH:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10]... | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2ccccn2)c(Cl)c1 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccco5)c34)cc2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 89 | [{"value": 89.0, "product": "ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 1.5 | HOUR | To a solution of ethyl 5-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate (300 mg) in 1-methyl-2-pyrrolidone (2.0 mL) was added 3-chloro-4-(pyridin-2-ylmethoxy)aniline (360 mg), and the mixture was heated to 140° C. and stirred for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, dilut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccoc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 1.5 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Cl)c32)o1.Nc1ccc(OCc2ccccn2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65b6906c23394a31be9fb8b1fbdbef01 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1>>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 | Cl.ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)OCC.O1CCCC1.[OH-].[Na+]>>ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][cH:28][n:29]5)[c:30]([Cl:31])[cH:32]4)[c:33]23)[o:34]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[cH:10][cH:11][c:12]3[n:13... | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 | O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 | null | null | O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccco5)c34)cc2)nc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 74.6 | [{"value": 74.6, "product": "ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(O2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of ethyl 5-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate (440 mg) in a mixed solvent of tetrahydrofuran (2.0 mL) and ethanol (2.0 mL) was added 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was stirred at room temperature for 5 hrs. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | Other | O.C(C)O | null | 5 | CCOC(=O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1>O.C(C)O>O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5ccccn5)c(Cl)c4)c32)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0593a72cc06840998137ea7460b90b2c | CCOC(=O)c1cc(N)ccc1Oc1cc(Cl)cc(Cl)c1.Clc1ncnc2cc[nH]c12>>CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 | ClC=1C2=C(N=CN1)C=CN2.NC=1C=CC(=C(C(=O)OCC)C1)OC1=CC(=CC(=C1)Cl)Cl>>ClC=1C=C(OC2=C(C(=O)OCC)C=C(C=C2)NC=2C3=C(N=CN2)C=CN3)C=C(C1)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][c:25]([Cl:26])[cH:27][c:28]([Cl:29])[cH:30]1.Cl[c:10]1[n:11][cH:12][n:13][c:14]2[cH:15][cH:16][nH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][nH:17... | CCOC(=O)c1cc(N)ccc1Oc1cc(Cl)cc(Cl)c1.Clc1ncnc2cc[nH]c12 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 84.6 | [{"value": 84.6, "product": "ClC=1C=C(OC2=C(C(=O)OCC)C=C(C=C2)NC=2C3=C(N=CN2)C=CN3)C=C(C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2.5 | HOUR | To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (61 mg) in 1-methyl-2-pyrrolidone (0.8 mL), was added ethyl 5-amino-2-(3,5-dichlorophenoxy)benzoate (186 mg), and the mixture was heated to 140° C. and stirred for 2.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 2.5 | CCOC(=O)c1cc(N)ccc1Oc1cc(Cl)cc(Cl)c1.Clc1ncnc2cc[nH]c12>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-faa4cab3877747e885404fcff18c5d88 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1>>O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 | Cl.ClC=1C=C(OC2=C(C(=O)OCC)C=C(C=C2)NC=2C3=C(N=CN2)C=CN3)C=C(C1)Cl.O1CCCC1.[OH-].[Na+]>>ClC=1C=C(OC2=C(C(=O)O)C=C(C=C2)NC=2C3=C(N=CN2)C=CN3)C=C(C1)Cl | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][nH:15][c:16]23)[cH:17][cH:18][c:19]1[O:20][c:21]1[cH:22][c:23]([Cl:24])[cH:25][c:26]([Cl:27])[cH:28]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][nH:15][c:16]23)[cH:17][cH:18][c:19]1[O... | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 | O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 | null | null | O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 81.1 | [{"value": 81.1, "product": "ClC=1C=C(OC2=C(C(=O)O)C=C(C=C2)NC=2C3=C(N=CN2)C=CN3)C=C(C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of ethyl 2-(3,5-dichlorophenoxy)-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoate (100 mg) in a mixed solvent of tetrahydrofuran (0.68 mL) and ethanol (0.68 mL) was added 1N aqueous sodium hydroxide solution (0.68 mL), and the mixture was stirred at room temperature for 16 hrs. 1N Hydrochloric acid (0.68 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | Other | O.C(C)O | null | 16 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1>O.C(C)O>O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1cc(Cl)cc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d84124ecc41478eb68773bd82261c72 | CCI.Clc1ncnc2cc[nH]c12>>CCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].ICC>>ClC=1C2=C(N=CN1)C=CN2CC | I[CH2:2][CH3:1].[nH:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([Cl:11])[c:12]12>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([Cl:11])[c:12]12 | CCI.Clc1ncnc2cc[nH]c12 | CCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1:2>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4](-[Cl;D1;H0:3]):[c:12]:2:1 | 79.1 | [{"value": 79.1, "product": "ClC=1C2=C(N=CN1)C=CN2CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg) in N,N-dimethylformamide (1.3 mL) was added potassium carbonate (269 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. Iodoethane (305 mg) was added to the reaction mixture, and the mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HI | O.CN(C=O)C | null | null | CCI.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3865050c042497a812c2daf532247a2 | CCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC | Cl[c:10]1[n:9][cH:8][n:7][c:6]2[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:28]21.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][c:22]([F:23])[cH:24]2)[c:25]([Cl:26])[cH:27]1>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:... | CCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 52.8 | [{"value": 52.8, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-5-ethyl-5H-pyrrolo[3,2-d]pyrimidine (85 mg) in 1-methyl-2-pyrrolidone (0.94 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (177 mg). The title compound (98 mg) was obtained as a pale-purple powder crystals by the reaction in the same manner as in Example 29.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | CN1C(CCC1)=O | null | null | CCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O>CCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6c84b33f0e041e3a58eb0e0d7f38cd5 | CCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>>CCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CC.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C>>C(C)N1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C | Cl[c:10]1[n:9][cH:8][n:7][c:6]2[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:27]21.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([CH3:21])[n:22][cH:23]2)[c:24]([CH3:25])[cH:26]1>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][c:17]4[cH:18][cH:19][c:2... | CCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1 | CCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 39.8 | [{"value": 39.8, "product": "C(C)N1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-5-ethyl-5H-pyrrolo[3,2-d]pyrimidine (85 mg) in 1-methyl-2-pyrrolidone (0.94 mL) was added 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (150 mg). The title compound (67 mg) was obtained as white powder crystals by the reaction in the same manner as in Example 29.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HCl | CN1C(CCC1)=O | null | null | CCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>CN1C(CCC1)=O>CCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f0c06619788479f8a64d0a7472d9305 | Clc1ncnc2cc[nH]c12.Nc1cccc(NC(=O)NCc2ccccc2)c1>>O=C(NCc1ccccc1)Nc1cccc(Nc2ncnc3cc[nH]c23)c1 | ClC=1C2=C(N=CN1)C=CN2.NC=1C=C(C=CC1)NC(=O)NCC1=CC=CC=C1>>C(C1=CC=CC=C1)NC(=O)NC1=CC(=CC=C1)NC=1C2=C(N=CN1)C=CN2 | Cl[c:18]1[n:19][cH:20][n:21][c:22]2[cH:23][cH:24][nH:25][c:26]12.[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:27]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([NH:17][c:18]2[n:19][cH:... | Clc1ncnc2cc[nH]c12.Nc1cccc(NC(=O)NCc2ccccc2)c1 | O=C(NCc1ccccc1)Nc1cccc(Nc2ncnc3cc[nH]c23)c1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(NCc1ccccc1)Nc1cccc(Nc2ncnc3cc[nH]c23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 41.6 | [{"value": 41.6, "product": "C(C1=CC=CC=C1)NC(=O)NC1=CC(=CC=C1)NC=1C2=C(N=CN1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 1.5 | HOUR | To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg) in 1-methyl-2-pyrrolidone (1.3 mL), was added N-(3-aminophenyl)-N′-benzylurea (220 mg), and the mixture was heated to 140° C. and stirred for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 1.5 | Clc1ncnc2cc[nH]c12.Nc1cccc(NC(=O)NCc2ccccc2)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>O=C(NCc1ccccc1)Nc1cccc(Nc2ncnc3cc[nH]c23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7959b1b4975645ba81c5467d367bf55b | NCCO.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>>O=C(NCCO)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)O)C=C2.Cl.CN(CCCN=C=NCC)C.ON1C(CCC1=O)=O.NCCO.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)NCCO)C=C2 | [NH2:3][CH2:4][CH2:5][OH:6].O[C:2](=[O:1])[c:7]1[cH:8][cH:9][c:10]([CH2:11][n:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]23)[cH:38][cH:39]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[c... | NCCO.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | O=C(NCCO)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccccc5)c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76.8 | [{"value": 76.8, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC2=CC=C(C(=O)NCCO)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 4-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoic acid (126 mg) in N,N-dimethylformamide (1.2 mL) were added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (72 mg) and 1-hydroxypyrrolidine-2,5-dione (43 mg), and the mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.CN(C=O)C | null | 3 | NCCO.O=C(O)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>O.CN(C=O)C>O=C(NCCO)c1ccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eadd9b22a18e4769b5ecf878d7f7f15e | CCOCCBr.Clc1ncnc2cc[nH]c12>>CCOCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCOCC>>ClC=1C2=C(N=CN1)C=CN2CCOCC | Br[CH2:5][CH2:4][O:3][CH2:2][CH3:1].[nH:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12 | CCOCCBr.Clc1ncnc2cc[nH]c12 | CCOCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:2>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 94.9 | [{"value": 94.9, "product": "ClC=1C2=C(N=CN1)C=CN2CCOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (500 mg) in N,N-dimethylformamide (4.5 mL) was added cesium carbonate (1324 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. 1-Bromo-2-ethoxyethane (1016 mg) was added to the reaction mixture, and the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CCOCCBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCOCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c61120ddc004022a087a9c366708edb | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCOCC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCC | Cl[c:13]1[n:12][cH:11][n:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])[c:31]21.[NH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([F:26])[cH:27]2)[c:28]([Cl:29])[cH:30]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[c... | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 51.2 | [{"value": 51.2, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 7 | HOUR | To a solution of 4-chloro-5-(2-ethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (90 mg) in 1-methyl-2-pyrrolidone (0.7 mL), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (151 mg) was added, and the mixture was heated to 140° C. and stirred for 7 hrs. The reaction mixture was allowed to cool to room temperature. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 7 | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f589859e47ab4ee292a820807646d4f8 | CI.Clc1ncnc2cc[nH]c12>>Cn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[K+].[K+].IC>>ClC=1C2=C(N=CN1)C=CN2C | I[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]12 | CI.Clc1ncnc2cc[nH]c12 | Cn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5bf74b4cd1577c88a528f020d69fbb295924bf4265fb986aea2d18f2c235ec34 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ncc2[nH]ccc2n1 | I-[CH3;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[nH;D2;+0:10]:[c:11]:2:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3](-[Cl;D1;H0:2]):[c:11]:2:1 | 93.1 | [{"value": 93.1, "product": "ClC=1C2=C(N=CN1)C=CN2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (320 mg) in N,N-dimethylformamide (2.0 mL), was added potassium carbonate (452 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. Iodomethane (444 mg) was added to the reaction mixture, and the mixture was stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HI | O.CN(C=O)C | null | null | CI.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>Cn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dac486025bf4490ea2c870eb0aa30ccd | Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2C.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2C | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][cH:3][n:2]([CH3:1])[c:27]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][c:21]([F:22])[cH:23]2)[c:24]([Cl:25])[cH:26]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20... | Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 53 | [{"value": 53.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 1.5 | HOUR | To a solution of 4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (100 mg) in 1-methyl-2-pyrrolidone (1.0 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (225 mg), and the mixture was heated to 140° C. and stirred for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 140 | 1.5 | Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ee2addd3ec74a60b158f1e5ea3cd0a9 | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1ccc2ncnc(Cl)c21>>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(C)c34)cc2C)cn1 | ClC=1C2=C(N=CN1)C=CN2C.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C>>CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:22][c:23]2[CH3:24])[cH:25][n:26]1.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][cH:18][n:19]([CH3:20])[c:21]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]4[cH:17][cH:18][n:19]([CH3:20])[c:21]... | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1ccc2ncnc(Cl)c21 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(C)c34)cc2C)cn1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 51.4 | [{"value": 51.4, "product": "CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (100 mg) in 1-methyl-2-pyrrolidone (1.0 mL) was added 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (192 mg). The title compound (106 mg) was obtained as white powder crystals by the reaction in the same manner as in Example 39 (ii).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccncc1.c1ccccc1.c1ncnc2cc[nH]c12 | HCl | CN1C(CCC1)=O | null | null | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1ccc2ncnc(Cl)c21>CN1C(CCC1)=O>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(C)c34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1b3355afb9a4ae08a2a4286f9f66d3b | CC(C)(C)[Si](C)(C)OCCI.Clc1ncnc2cc[nH]c12>>CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)(C)[Si](C)(C)OCCI>>[Si](C)(C)(C(C)(C)C)OCCN1C=CC=2N=CN=C(C21)Cl | I[CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[nH:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12 | CC(C)(C)[Si](C)(C)OCCI.Clc1ncnc2cc[nH]c12 | CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 94.8 | [{"value": 94.8, "product": "[Si](C)(C)(C(C)(C)C)OCCN1C=CC=2N=CN=C(C21)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) in N,N-dimethylformamide (2.0 mL) was added cesium carbonate (977 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added tert-butyl(2-iodoethoxy)dimethylsilane (839 mg), and the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HI | O.CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)OCCI.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ab98b28434e43a4b3f45e237b938e87 | CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21>>OCCn1ccc2ncnc(Cl)c21 | [Si](C)(C)(C(C)(C)C)OCCN1C=CC=2N=CN=C(C21)Cl.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>ClC=1C2=C(N=CN1)C=CN2CCO | CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12>>[OH:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12 | CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21 | OCCn1ccc2ncnc(Cl)c21 | null | null | O1CCCC1.O | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ncc2[nH]ccc2n1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 110.2 | [{"value": 110.2, "product": "ClC=1C2=C(N=CN1)C=CN2CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (560 mg) in tetrahydrofuran (1.7 mL), was added tetrabutylammonium fluoride (1M tetrahydrofuran solution) (2.69 mL) under ice-cooling, and the mixture was stirred for 4 hrs. The reaction mixture was diluted with water (20 ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ncnc2cc[nH]c12 | Other | O1CCCC1.O | null | 4 | CC(C)(C)[Si](C)(C)OCCn1ccc2ncnc(Cl)c21>O1CCCC1.O>OCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71e2d5916b8f49d3be0669749205c538 | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCCn1ccc2ncnc(Cl)c21>>OCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | C(C)(=O)OCC.ClC=1C2=C(N=CN1)C=CN2CCO.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCO | [NH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]2)[c:26]([Cl:27])[cH:28]1.Cl[c:11]1[n:10][cH:9][n:8][c:7]2[cH:6][cH:5][n:4]([CH2:3][CH2:2][OH:1])[c:29]21>>[OH:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH2:... | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCCn1ccc2ncnc(Cl)c21 | OCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 75.9 | [{"value": 75.9, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | To a solution of 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethanol (130 mg) in 1-methyl-2-pyrrolidone (1.3 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (193 mg), and the reaction mixture was stirred at 120° C. for 2 hrs. The reaction mixture was allowed to cool to room temperature and ethyl acetate (20 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | CN1C(CCC1)=O | 120 | 2 | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.OCCn1ccc2ncnc(Cl)c21>CN1C(CCC1)=O>OCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8912d900096a459d8f3ace15cc22d79a | CCCBr.Clc1ncnc2cc[nH]c12>>CCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCC>>ClC=1C2=C(N=CN1)C=CN2CCC | Br[CH2:3][CH2:2][CH3:1].[nH:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12 | CCCBr.Clc1ncnc2cc[nH]c12 | CCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:2>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 84.2 | [{"value": 84.2, "product": "ClC=1C2=C(N=CN1)C=CN2CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in N,N-dimethylformamide (1.6 mL) was added cesium carbonate (798 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 1-bromopropane (301 mg), and the mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CCCBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac3c1030d70b4c1380b61eccb5781071 | CCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCC | Cl[c:11]1[n:10][cH:9][n:8][c:7]2[cH:6][cH:5][n:4]([CH2:3][CH2:2][CH3:1])[c:29]21.[NH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]2)[c:26]([Cl:27])[cH:28]1>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH... | CCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 57.1 | [{"value": 57.1, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | To a solution of 4-chloro-5-propyl-5H-pyrrolo[3,2-d]pyrimidine (80 mg) in 1-methyl-2-pyrrolidone (0.8 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (193 mg), and the reaction mixture was stirred at 120° C. for 2 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 120 | 2 | CCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a35c64370fce46cc9a8074af65db6f3d | CC(C)CBr.Clc1ncnc2cc[nH]c12>>CC(C)Cn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(C)C>>ClC=1C2=C(N=CN1)C=CN2CC(C)C | Br[CH2:4][CH:2]([CH3:1])[CH3:3].[nH:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([Cl:13])[c:14]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([Cl:13])[c:14]12 | CC(C)CBr.Clc1ncnc2cc[nH]c12 | CC(C)Cn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1:2>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]2:[#7;a:9]:[c:8]:[#7;a:7]:[c:6](-[Cl;D1;H0:5]):[c:14]:2:1 | 102.5 | [{"value": 102.5, "product": "ClC=1C2=C(N=CN1)C=CN2CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in N,N-dimethylformamide (1.6 mL) was added cesium carbonate (478 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 1-bromo-2-methylpropane (336 mg), and the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CC(C)CBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CC(C)Cn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1af6b08c45f54bfca40b81075bc3390d | BrCC1CCCO1.Clc1ncnc2cc[nH]c12>>Clc1ncnc2ccn(CC3CCCO3)c12 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCC1OCCC1>>ClC=1C2=C(N=CN1)C=CN2CC2OCCC2 | Br[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][O:15]1.[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][cH:8][nH:9][c:16]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][cH:8][n:9]([CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][O:15]3)[c:16]12 | BrCC1CCCO1.Clc1ncnc2cc[nH]c12 | Clc1ncnc2ccn(CC3CCCO3)c12 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2c(ccn2CC2CCCO2)n1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5].[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[nH;D2;+0:14]:[c:15]:1:2>>[C:3]-[C:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7](-[Cl;D1;H0:6]):[c:15]:2:1)-[#8:4]-[C:5] | 86.1 | [{"value": 86.1, "product": "ClC=1C2=C(N=CN1)C=CN2CC2OCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in N,N-dimethylformamide (1.0 mL) was added cesium carbonate (478 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-(bromomethyl)tetrahydrofuran (242 mg), and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.C1CCOC1 | HBr | O.CN(C=O)C | null | null | BrCC1CCCO1.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>Clc1ncnc2ccn(CC3CCCO3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ee4b6defa4449d0873f4d7e722d8845 | COC(=O)c1cccc(CBr)c1.Clc1ncnc2cc[nH]c12>>COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCC=1C=C(C(=O)OC)C=CC1>>ClC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2 | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21]1.[nH:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[cH:12][cH:13][c:14]3[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]23)[cH:21]1 | COC(=O)c1cccc(CBr)c1.Clc1ncnc2cc[nH]c12 | COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ncncc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:1>>[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:14]:2:1 | 54.1 | [{"value": 54.1, "product": "ClC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (300 mg) in N,N-dimethylformamide (2.0 mL) was added cesium carbonate (955 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added methyl 3-(bromomethyl)benzoate (671 mg), and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | COC(=O)c1cccc(CBr)c1.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a846403657914eb1b1e28cee4ab548cb | COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 | ClC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2 | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][c:9]3[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:37]3)[c:36]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]2)[c:33]([Cl:34])[cH:35]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([... | COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccccc5)c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 89.6 | [{"value": 89.6, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1.5 | HOUR | To a solution of methyl 3-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]benzoate (670 mg) in 1-methyl-2-pyrrolidone (3.0 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (549 mg), and the reaction mixture was stirred at 120° C. for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 120 | 1.5 | COC(=O)c1cccc(Cn2ccc3ncnc(Cl)c32)c1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2285d8165eb40c08165abfd88ccf1b0 | COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1>>O=C(O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 | Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)OC)C=CC2.O1CCCC1.[OH-].[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)O)C=CC2 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[c:32]([Cl:33])[cH:34]4)[c:35]23)[cH:36]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:... | COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 | O=C(O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccn(Cc5ccccc5)c34)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 78.4 | [{"value": 78.4, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC=2C=C(C(=O)O)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of methyl 3-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoate (800 mg) in a mixed solvent of tetrahydrofuran (4.0 mL) and methanol (4.0 mL) was added 1N aqueous sodium hydroxide solution (4.0 mL), and the mixture was stirred at room temperature for 12 hrs.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | O.CO | null | 12 | COC(=O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1>O.CO>O=C(O)c1cccc(Cn2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af73e68d64c447fda2f1e598bbd4b33d | CCOCCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>>CCOCCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCOCC.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C>>C(C)OCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C | Cl[c:13]1[n:12][cH:11][n:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])[c:30]21.[NH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][c:20]2[cH:21][cH:22][c:23]([CH3:24])[n:25][cH:26]2)[c:27]([CH3:28])[cH:29]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][... | CCOCCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1 | CCOCCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 66.8 | [{"value": 66.8, "product": "C(C)OCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | To a solution of 4-chloro-5-(2-ethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (160 mg) in 1-methyl-2-pyrrolidone (1.4 mL) was added 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (228 mg), and the reaction mixture was stirred at 120° C. for 2 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 120 | 2 | CCOCCn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOCCn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c549748491a4043be9951f2fb8a73be | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2ccccn2)c(Cl)c1>>CCOCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCOCC.ClC=1C=C(N)C=CC1OCC1=NC=CC=C1>>ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CCOCC | Cl[c:13]1[n:12][cH:11][n:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])[c:30]21.[NH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[c:27]([Cl:28])[cH:29]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH... | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2ccccn2)c(Cl)c1 | CCOCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 53.2 | [{"value": 53.2, "product": "ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=CN2CCOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-5-(2-ethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (160 mg) in 1-methyl-2-pyrrolidone (1.4 mL) was added 3-chloro-4-(pyridin-2-ylmethoxy)aniline (250 mg). The title compound (160 mg) was obtained as pale-yellow needle crystals by the reaction in the same manner as in Example 42 (ii).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HCl | CN1C(CCC1)=O | null | null | CCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2ccccn2)c(Cl)c1>CN1C(CCC1)=O>CCOCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae288ca3a3cf4c82b267bc4f518883c6 | Clc1ncnc2cc[nH]c12.FCCBr>>FCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCF>>ClC=1C2=C(N=CN1)C=CN2CCF | [nH:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12.Br[CH2:3][CH2:2][F:1]>>[F:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][n:10][c:11]([Cl:12])[c:13]12 | Clc1ncnc2cc[nH]c12.FCCBr | FCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:2>>[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3]):[c:13]:1:2 | 84.6 | [{"value": 84.6, "product": "ClC=1C2=C(N=CN1)C=CN2CCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg) in N,N-dimethylformamide (0.6 mL) was added cesium carbonate (281 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 1-bromo-2-fluoroethane (124 mg), and the mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | Clc1ncnc2cc[nH]c12.FCCBr>O.CN(C=O)C>FCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb3778ac0e464ea3a0e98d0b215f25a3 | CCOC(=O)CBr.Clc1ncnc2cc[nH]c12>>CCOC(=O)Cn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC>>ClC=1C2=C(N=CN1)C=CN2CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]12 | CCOC(=O)CBr.Clc1ncnc2cc[nH]c12 | CCOC(=O)Cn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6c94e785ea287624ec6e807461cf2b4f21051c0d5237d4978c0a9b50260bba0a | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[nH;D2;+0:14]:[c:15]:2:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]2:[#7;a:10]:[c:9]:[#7;a:8]:[c:7](-[Cl;D1;H0:6]):[c:15]:2:1 | 67.3 | [{"value": 67.3, "product": "ClC=1C2=C(N=CN1)C=CN2CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg) in N,N-dimethylformamide (1.3 mL) was added cesium carbonate (615 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added ethyl bromoacetate (326 mg), and the mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CCOC(=O)CBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCOC(=O)Cn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-385d48fc52af48e984fd4154ad554256 | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>>CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CC(=O)OCC.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C>>C(C)OC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)=O | Cl[c:14]1[n:13][cH:12][n:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:31]21.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][c:24]([CH3:25])[n:26][cH:27]2)[c:28]([CH3:29])[cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([NH:15][... | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1 | CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | null | null | C(O)([O-])=O.[Na+].C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[#8:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:13]:1:2 | 86.1 | [{"value": 86.1, "product": "C(C)OC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 2 | HOUR | To a solution of ethyl (4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)acetate (140 mg) in isopropyl alcohol (0.6 mL) was added 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (188 mg), and the mixture was stirred in an oil bath at a temperature of 110° C. for 2 hrs. The reaction mixture was allowed to cool to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HCl | C(O)([O-])=O.[Na+].C(C)(C)O | 110 | 2 | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>C(O)([O-])=O.[Na+].C(C)(C)O>CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca7b932d10934bc78f79606ec5e7128b | CC(C)(C)[Si](C)(C)OCCCBr.Clc1ncnc2cc[nH]c12>>CC(C)(C)[Si](C)(C)OCCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCCO[Si](C)(C)C(C)(C)C>>[Si](C)(C)(C(C)(C)C)OCCCN1C=CC=2N=CN=C(C21)Cl | Br[CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[nH:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][n:18][c:19]([Cl:20])[c:21]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][n:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][n:18][c:19]([Cl:20])[c:21]12 | CC(C)(C)[Si](C)(C)OCCCBr.Clc1ncnc2cc[nH]c12 | CC(C)(C)[Si](C)(C)OCCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 74.2 | [{"value": 74.2, "product": "[Si](C)(C)(C(C)(C)C)OCCCN1C=CC=2N=CN=C(C21)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (400 mg) in N,N-dimethylformamide (2.6 mL) was added cesium carbonate (957 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added (3-bromopropoxy)(tert-butyl)dimethylsilane (979 mg), and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)OCCCBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CC(C)(C)[Si](C)(C)OCCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ccb671408254f98a5fda480c7060e25 | Clc1ncnc2cc[nH]c12.FC(F)(F)CCCBr>>FC(F)(F)CCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCCC(F)(F)F>>ClC=1C2=C(N=CN1)C=CN2CCCC(F)(F)F | [nH:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]12.Br[CH2:7][CH2:6][CH2:5][C:2]([F:1])([F:3])[F:4]>>[F:1][C:2]([F:3])([F:4])[CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]12 | Clc1ncnc2cc[nH]c12.FC(F)(F)CCCBr | FC(F)(F)CCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 102.5 | [{"value": 102.5, "product": "ClC=1C2=C(N=CN1)C=CN2CCCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (250 mg) in N,N-dimethylformamide (1.6 mL) was added cesium carbonate (675 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 4-bromo-1,1,1-trifluorobutane (466 mg), and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | Clc1ncnc2cc[nH]c12.FC(F)(F)CCCBr>O.CN(C=O)C>FC(F)(F)CCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-067ac7b4543344aaa869db9cdbbb9194 | CCOCCOCCBr.Clc1ncnc2cc[nH]c12>>CCOCCOCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCCOCCOCC>>ClC=1C2=C(N=CN1)C=CN2CCOCCOCC | Br[CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH3:1].[nH:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12 | CCOCCOCCBr.Clc1ncnc2cc[nH]c12 | CCOCCOCCn1ccc2ncnc(Cl)c21 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 83.5 | [{"value": 83.5, "product": "ClC=1C2=C(N=CN1)C=CN2CCOCCOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (300 mg) in N,N-dimethylformamide (2.0 mL) was added cesium carbonate (728 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 1-bromo-2-(2-ethoxyethoxy)ethane (496 mg), and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O.CN(C=O)C | null | null | CCOCCOCCBr.Clc1ncnc2cc[nH]c12>O.CN(C=O)C>CCOCCOCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2efab3c64a44496bb732c531c5e493df | CCOCCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCOCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCOCCOCC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCCOCC | Cl[c:16]1[n:15][cH:14][n:13][c:12]2[cH:11][cH:10][n:9]([CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH3:1])[c:34]21.[NH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]2)[c:31]([Cl:32])[cH:33]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12... | CCOCCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCOCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 54.1 | [{"value": 54.1, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCCOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1 | HOUR | To a solution of 4-chloro-5-[2-(2-ethoxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in 1-methyl-2-pyrrolidone (1.1 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (189 mg), and the reaction mixture was stirred at 120° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, diluted with 5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 120 | 1 | CCOCCOCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>CCOCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b99d03249c546ccbf009a09b48b2bab | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCO)c34)cc2C)cn1>>Cc1ccc(Oc2ccc(N3CCn4ccc5ncnc3c54)cc2C)cn1 | CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=CN2CCO.C(CCC)P(CCCC)CCCC.N(=N\C(=O)N1CCCCC1)/C(=O)N1CCCCC1>>CC=1C=C(C=CC1OC=1C=NC(=CC1)C)N1CCN2C3=C(N=CN=C13)C=C2 | O[CH2:12][CH2:13][n:14]1[cH:15][cH:16][c:17]2[n:18][cH:19][n:20][c:21]([NH:11][c:10]3[cH:9][cH:8][c:7]([O:6][c:5]4[cH:4][cH:3][c:2]([CH3:1])[n:27][cH:26]4)[c:24]([CH3:25])[cH:23]3)[c:22]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][n:14]4[cH:15][cH:16][c:17]5[n:18][cH:19][n:20... | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCO)c34)cc2C)cn1 | Cc1ccc(Oc2ccc(N3CCn4ccc5ncnc3c54)cc2C)cn1 | null | null | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 83972de9d5aeac1a8f9201b9dcbe455b9704eb65f35518baa50eeca5c47387c2 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1cncc(Oc2ccc(N3CCn4ccc5ncnc3c54)cc2)c1 | O-[CH2;D2;+0:1]-[C:2]-[#7;a:3](:[c:4]):[c:5]1:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[c:4]:[#7;a:3]1:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2-[N;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])-[CH2;D2;+0:1]-[C:2]-1 | 75.6 | [{"value": 75.6, "product": "CC=1C=C(C=CC1OC=1C=NC(=CC1)C)N1CCN2C3=C(N=CN=C13)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of 2-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethanol (50 mg) and tributylphosphine (54 mg) in toluene (2.5 mL) was added 1,1′-[(E)-diazene-1,2-diyldicarbonyl]dipiperidine (67 mg), and the mixture was stirred at room temperature for 3 hrs. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | c1nc2c3c(ccn3CC[NH]2)n1 | c1ccncc1.c1ccccc1.c1nc2c3c(ccn3CC[NH]2)n1 | HO- | O.C1(=CC=CC=C1)C | null | 3 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCO)c34)cc2C)cn1>O.C1(=CC=CC=C1)C>Cc1ccc(Oc2ccc(N3CCn4ccc5ncnc3c54)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39357e8768c7471a8bd07f459e37468c | CCOC(=O)c1cccc(N)c1.Clc1ncnc2cc[nH]c12>>CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | ClC=1C2=C(N=CN1)C=CN2.NC=1C=C(C(=O)OCC)C=CC1.CN1C(CCC1)=O.C(O)([O-])=O.[Na+]>>N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)OCC)C=CC2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:21]1.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][cH:18][nH:19][c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][n:15][c:16]3[cH:17][cH:18][nH:19][c:20]23)[cH:21]1 | CCOC(=O)c1cccc(N)c1.Clc1ncnc2cc[nH]c12 | CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3cc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 55.8 | [{"value": 55.8, "product": "N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)OCC)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1.5 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (2.78 g), ethyl 3-aminobenzoate (4.49 g) and 1-methyl-2-pyrrolidone (20 mL) was stirred at 120° C. for 1.5 hrs. To the reaction mixture were added ethyl acetate, water and saturated aqueous sodium hydrogen carbonate solution. The insoluble material was filtered off, and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1 | HCl | O.C(C)(=O)OCC | 120 | 1.5 | CCOC(=O)c1cccc(N)c1.Clc1ncnc2cc[nH]c12>O.C(C)(=O)OCC>CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-240d07a3cd4f4b5f82d57410f500c678 | CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1>>O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)OCC)C=CC2.[OH-].[Na+].Cl>>N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][nH:17][c:18]23)[cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][nH:17][c:18]23)[cH:19]1 | CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ncnc3cc[nH]c23)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 102.7 | [{"value": 102.7, "product": "N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of ethyl 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoate (3.34 g), 1N aqueous sodium hydroxide solution (25 mL) and methanol (50 mL) was stirred overnight at room temperature. To the reaction mixture was added 1N hydrochloric acid (25 mL), and methanol was evaporated under reduced pressure. The precipitated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncc2[nH]ccc2n1 | Other | CO | null | 8 | CCOC(=O)c1cccc(Nc2ncnc3cc[nH]c23)c1>CO>O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfff2fd8eaad455883e09882bfbe82d6 | C1CCNCC1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCCCC1 | ON1N=NC2=C1C=CC=C2.N1CCCCC1.Cl.CN(CCCN=C=NCC)C.N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2.N1CCCCC1.Cl.CN(CCCN=C=NCC)C>>N1(CCCCC1)C(=O)C=1C=C(C=CC1)NC=1C2=C(N=CN1)C=CN2 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][nH:16][c:17]23)[cH:18]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][nH:16][c:17]23)[cH:18]1)[N:19]1[CH2:20][CH2:21][CH2:2... | C1CCNCC1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCCCC1 | null | null | [Cl-].[Na+].O.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | null | [] | null | null | 2 | HOUR | A mixture of 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (153 mg), piperidine (0.078 mL), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hrs. Piperidine (0.078 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ncc2[nH]ccc2n1.C1CC[NH]CC1 | HO- | [Cl-].[Na+].O.CN(C=O)C | null | 2 | C1CCNCC1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>[Cl-].[Na+].O.CN(C=O)C>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-670f85c4b0dd4990b1819bec16530819 | C1CSCCN1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCSCC1 | ON1N=NC2=C1C=CC=C2.N1CCSCC1.Cl.CN(CCCN=C=NCC)C.N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2.N1CCSCC1.Cl.CN(CCCN=C=NCC)C>>N1(CCSCC1)C(=O)C=1C=C(C=CC1)NC=1C2=C(N=CN1)C=CN2 | [NH:19]1[CH2:20][CH2:21][S:22][CH2:23][CH2:24]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][nH:16][c:17]23)[cH:18]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][nH:16][c:17]23)[cH:18]1)[N:19]1[CH2:20][CH2:21][S:22][C... | C1CSCCN1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCSCC1 | null | null | [Cl-].[Na+].O.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 592ef6f3ea027639e6c15db529b85acc14b91923fdff2065727707555f3732c7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCSCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#16:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#16:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | A mixture of 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (153 mg), thiomorpholine (0.091 mL), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hrs. Thiomorpholine (0.030 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CSCCN1 | C1CSCC[NH]1 | c1ccccc1.c1ncc2[nH]ccc2n1.C1CSCC[NH]1 | HO- | [Cl-].[Na+].O.CN(C=O)C | null | 2 | C1CSCCN1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>[Cl-].[Na+].O.CN(C=O)C>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCSCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c80f3cb108714be381d6dca24574dc2e | O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1.c1ccc(CC2CCNCC2)cc1>>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCC(Cc2ccccc2)CC1 | N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2.C(C1=CC=CC=C1)C1CCNCC1.Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2>>C(C1=CC=CC=C1)C1CCN(CC1)C(=O)C=1C=C(C=CC1)NC=1C2=C(N=CN1)C=CN2 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][nH:16][c:17]23)[cH:18]1.[NH:19]1[CH2:20][CH2:21][CH:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][n... | O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1.c1ccc(CC2CCNCC2)cc1 | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCC(Cc2ccccc2)CC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCC(Cc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | 81.2 | [{"value": 81.2, "product": "C(C1=CC=CC=C1)C1CCN(CC1)C(=O)C=1C=C(C=CC1)NC=1C2=C(N=CN1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (153 mg), 4-benzylpiperidine (158 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg), 1-hydroxybenzotriazole (138 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 hrs. The reaction mixture was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ncc2[nH]ccc2n1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C=O)C | null | 3 | O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1.c1ccc(CC2CCNCC2)cc1>CN(C=O)C>O=C(c1cccc(Nc2ncnc3cc[nH]c23)c1)N1CCC(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-daf51b578f654598b965018c5face7ff | NCc1ccccc1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>>O=C(NCc1ccccc1)c1cccc(Nc2ncnc3cc[nH]c23)c1 | N1=CN=C(C2=C1C=CN2)NC=2C=C(C(=O)O)C=CC2.C(C1=CC=CC=C1)N.Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2>>C(C1=CC=CC=C1)NC(C1=CC(=CC=C1)NC=1C2=C(N=CN1)C=CN2)=O | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][c:15]([NH:16][c:17]2[n:18][cH:19][n:20][c:21]3[cH:22][cH:23][nH:24][c:25]23)[cH:26]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([NH:16][c:17]2[n:18][cH:19][n:20][c:21]... | NCc1ccccc1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1 | O=C(NCc1ccccc1)c1cccc(Nc2ncnc3cc[nH]c23)c1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1cccc(Nc2ncnc3cc[nH]c23)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 61.9 | [{"value": 61.9, "product": "C(C1=CC=CC=C1)NC(C1=CC(=CC=C1)NC=1C2=C(N=CN1)C=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (153 mg), benzylamine (96 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (173 mg), 1-hydroxybenzotriazole (138 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 days. The reaction mixture was concentrated und... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1 | HO- | CN(C=O)C | null | 72 | NCc1ccccc1.O=C(O)c1cccc(Nc2ncnc3cc[nH]c23)c1>CN(C=O)C>O=C(NCc1ccccc1)c1cccc(Nc2ncnc3cc[nH]c23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fad64d0f1a4e45a4b69194a647c21ad6 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(CO)c1>>OCc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | ClC=1C2=C(N=CN1)C=CN2.NC=1C=CC(=C(C1)CO)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)CO | Cl[c:7]1[n:8][cH:9][n:10][c:11]2[cH:12][cH:13][nH:14][c:15]12.[OH:1][CH2:2][c:3]1[cH:4][c:5]([NH2:6])[cH:16][cH:17][c:18]1[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][nH:14][c:15]23)[cH:16][cH:17][c:18]1[O:19][CH2:20][c:21]1... | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(CO)c1 | OCc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 40.3 | [{"value": 40.3, "product": "C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg), [5-amino-2-(benzyloxy)phenyl]methanol (459 mg) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added and the mixture was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | CN(C=O)C | 80 | 4 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(CO)c1>CN(C=O)C>OCc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc3f968d5e284d2d81428d6a5969d4f0 | COc1cc(N)ccc1OCc1ccccc1.Clc1ncnc2cc[nH]c12>>COc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | ClC=1C2=C(N=CN1)C=CN2.C(C1=CC=CC=C1)OC1=C(C=C(N)C=C1)OC.CN1C(CCC1)=O>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:16][cH:17][c:18]1[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.Cl[c:7]1[n:8][cH:9][n:10][c:11]2[cH:12][cH:13][nH:14][c:15]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][nH:14][c:15]23)[cH:16][cH:17][c:18]1[O:19][CH2:20][c:21]1[c... | COc1cc(N)ccc1OCc1ccccc1.Clc1ncnc2cc[nH]c12 | COc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 59.7 | [{"value": 59.7, "product": "C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg), 4-(benzyloxy)-3-methoxyaniline (298 mg) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 80° C. for 4 hrs. Methanol and activated carbon were added to the reaction mixture and the mixture was stirred. The activated carbon was filtered off, aqueous sodium hydro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | CO | 80 | 4 | COc1cc(N)ccc1OCc1ccccc1.Clc1ncnc2cc[nH]c12>CO>COc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69cd76e25f794ae5ae52dfdfac3d9ec8 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(Cl)c1>>Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | ClC=1C2=C(N=CN1)C=CN2.C(C1=CC=CC=C1)OC1=C(C=C(N)C=C1)Cl.CN1C(CCC1)=O>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)Cl | Cl[c:6]1[n:7][cH:8][n:9][c:10]2[cH:11][cH:12][nH:13][c:14]12.[Cl:1][c:2]1[cH:3][c:4]([NH2:5])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][cH:12][nH:13][c:14]23)[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][c... | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(Cl)c1 | Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 49.5 | [{"value": 49.5, "product": "C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg), 4-(benzyloxy)-3-chloroaniline (365 mg) and 1-methyl-2-pyrrolidone (3 mL) was stirred at 80° C. for 4 hrs. Methanol and activated carbon were added to the reaction mixture and the mixture was stirred. The activated carbon was filtered off, aqueous sodium hydrog... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | CO | 80 | 4 | Clc1ncnc2cc[nH]c12.Nc1ccc(OCc2ccccc2)c(Cl)c1>CO>Clc1cc(Nc2ncnc3cc[nH]c23)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdd7838e037f4837b5b2452a5e403701 | CCO.CCc1nc(Cl)c2[nH]ccc2n1.Nc1ccc(Oc2ccccc2)c(C(=O)[O-])c1>>CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | C(C)C=1N=C(C2=C(N1)C=CN2)Cl.NC=1C=CC(=C(C(=O)[O-])C1)OC1=CC=CC=C1.CN1C(CCC1)=O.C(C)O>>O(C1=CC=CC=C1)C1=C(C(=O)OCC)C=C(C=C1)NC=1C2=C(N=CN1)C=CN2 | O[CH2:2][CH3:1].CC[c:12]1[n:11][c:10](Cl)[c:18]2[c:14]([n:13]1)[cH:15][cH:16][nH:17]2.[O-:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][nH:17][c:18]2... | CCO.CCc1nc(Cl)c2[nH]ccc2n1.Nc1ccc(Oc2ccccc2)c(C(=O)[O-])c1 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b5bc02a189a8a2933e820f699bd5b360f72326a156ac3a6d1bded089e3b5c856 | e2f3e76b9378ab2fa98631319547fb730cc7f03b13d2ec9dd6ca62bd7cba28be | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4]2:[#7;a:5]:[c:6]:[c:7]:[c:8]:2:[#7;a:9]:1.O-[CH2;D2;+0:10]-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]:[c:16]-[C:17](-[O-;H0;D1:18])=[O;D1;H0:19]>>[C;D1;H3:11]-[CH2;D2;+0:10]-[O;H0;D2;+0:18]-[C:17](=[O;D1;H0:19])-[c:16]:[c:15]:[c:13](-[NH;D2;+0:12]-[c;H0;D3;+... | null | [] | 80 | CELSIUS | 2 | HOUR | A mixture of ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (461 mg), 5-amino-2-phenoxybenzoate (926 mg) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 80° C. for 2 hrs. Ethanol, water and activated carbon were added to the reaction mixture and the mixture was stirred. The activated carbon was filtered off, and the solve... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Primary amine | Ester.Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | O | 80 | 2 | CCO.CCc1nc(Cl)c2[nH]ccc2n1.Nc1ccc(Oc2ccccc2)c(C(=O)[O-])c1>O>CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8b70c4375f04973a2417d592922d457 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1>>O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | O(C1=CC=CC=C1)C1=C(C(=O)OCC)C=C(C=C1)NC=1C2=C(N=CN1)C=CN2.[OH-].[Na+].Cl>>O(C1=CC=CC=C1)C1=C(C(=O)O)C=C(C=C1)NC=1C2=C(N=CN1)C=CN2 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][nH:15][c:16]23)[cH:17][cH:18][c:19]1[O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][nH:15][c:16]23)[cH:17][cH:18][c:19]1[O:20][c:21]1[cH:2... | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 92.3 | [{"value": 92.3, "product": "O(C1=CC=CC=C1)C1=C(C(=O)O)C=C(C=C1)NC=1C2=C(N=CN1)C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1.5 | HOUR | A mixture of ethyl 2-phenoxy-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoate (899 mg), 1N aqueous sodium hydroxide solution (5 mL) and methanol (15 mL) was stirred at 60° C. for 1.5 hrs. To the reaction mixture was added 1N hydrochloric acid (5 mL), and methanol was evaporated under reduced pressure. The precipitated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | Other | CO | 60 | 1.5 | CCOC(=O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1>CO>O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e377384a0c74bea8556a6adfb81f9a4 | O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1>>OCc1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | CO.[BH4-].[Na+].O(C1=CC=CC=C1)C1=C(C(=O)O)C=C(C=C1)NC=1C2=C(N=CN1)C=CN2.C(=O)(N1C=NC=C1)N1C=NC=C1>>O(C1=CC=CC=C1)C1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)CO | O[C:2](=[O:1])[c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][nH:14][c:15]23)[cH:16][cH:17][c:18]1[O:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][nH:14][c:15]23)[cH:16][cH:17][c:18]1[O:19][c:20]1[cH:21][cH:22][cH:2... | O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | OCc1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 | null | null | O.CN(C=O)C | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 26.5 | [{"value": 26.5, "product": "O(C1=CC=CC=C1)C1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-phenoxy-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoic acid (173 mg) in N,N-dimethylformamide (5 mL) was added 1,1′-carbonyldiimidazole (97 mg) and the mixture was stirred at room temperature for 1 hr. Sodium borohydride (38 mg) was added to the reaction mixture at room temperature, and methanol (1 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | Other | O.CN(C=O)C | null | 1 | O=C(O)c1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1>O.CN(C=O)C>OCc1cc(Nc2ncnc3cc[nH]c23)ccc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8cb0c29e4c24630a8584314d898a303 | Cc1ccc(S(=O)(=O)Cl)cc1.N#CCC(=O)c1ccco1>>Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1 | O1C(=CC=C1)C(CC#N)=O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)N(CC)CC>>CC1=CC=C(C=C1)S(=O)(=O)OC(=CC#N)C=1OC=CC1 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)(=[O:7])=[O:8].[O:9]=[C:10]([CH2:11][C:12]#[N:13])[c:14]1[cH:15][cH:16][cH:17][o:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][C:10](=[CH:11][C:12]#[N:13])[c:14]2[cH:15][cH:16][cH:17][o:18]2)[cH:19][cH:20]1 | Cc1ccc(S(=O)(=O)Cl)cc1.N#CCC(=O)c1ccco1 | Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 9f8c97f001bd09a5896e1620aa92ed222c76fd261d4582b923c7f486d025fb40 | ad2bf1a301061ff4de8cacf445aa6c9f6615e0daaa746ef88ba96d39fc5112df | [CH]=C(OS(=O)(=O)c1ccccc1)c1ccco1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[#8;a:14]:[c:15]>>[N;D1;H0:7]#[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:10](-[O;H0;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[c:12](:[c:13]):[#8;a:14]:... | 92.5 | [{"value": 92.5, "product": "CC1=CC=C(C=C1)S(=O)(=O)OC(=CC#N)C=1OC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-(2-furyl)-3-oxopropanenitrile (5.29 g), p-toluenesulfonyl chloride (9.00 g) and dichloromethane (60 mL) was added dropwise triethylamine (5.99 g) under ice-cooling. After stirring under ice-cooling for 1.5 hrs, the mixture was diluted with dichloromethane (100 mL). The mixture washed with water (150 m... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccoc1 | HCl | ClCCl | null | null | Cc1ccc(S(=O)(=O)Cl)cc1.N#CCC(=O)c1ccco1>ClCCl>Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62e715fe296147099d7127fe67836a60 | CCOC(=O)C(N)C(=O)OCC.Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1>>CCOC(=O)c1[nH]c(-c2ccco2)cc1N | CC1=CC=C(C=C1)S(=O)(=O)OC(=CC#N)C=1OC=CC1.Cl.NC(C(=O)OCC)C(=O)OCC.[O-]CC.[Na+].Cl>>NC1=C(NC(=C1)C=1OC=CC1)C(=O)OCC | CCOC(=O)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH2:7].Cc1ccc(S(=O)(=O)O[C:8]([c:9]2[cH:10][cH:11][cH:12][o:13]2)=[CH:14][C:15]#[N:16])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][o:13]2)[cH:14][c:15]1[NH2:16] | CCOC(=O)C(N)C(=O)OCC.Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1 | CCOC(=O)c1[nH]c(-c2ccco2)cc1N | null | null | O1CCCC1.C(C)O | Functional Group Interconversion | OtherReaction | d25017a4cc1663869a2ad8f70e12ba7e816f6e3bcd1c9ef62cf784d611fc306c | 2761e1a6469897982b9f37673b7247d314aab4379d45b535816ae836a29bb8eb | c1c[nH]c(-c2ccco2)c1 | C-C-O-C(=O)-[CH;D3;+0:1](-[NH2;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].C-c1:c:c:c(-S(=O)(=O)-O-[C;H0;D3;+0:7](=[CH;D2;+0:8]-[C;H0;D2;+0:9]#[N;H0;D1;+0:10])-[c;H0;D3;+0:11]2:[#8;a:12]:[c:13]:[c:14]:[c:15]:2):c:c:1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c;H0;D3;+0:7](-[c;H0;D3;+0:11]2:[#8;a:12... | 33.3 | [{"value": 33.3, "product": "NC1=C(NC(=C1)C=1OC=CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 2-cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate (10.48 g) and diethyl aminomalonate hydrochloride (7.67 g) in a mixed solvent of ethanol (120 mL)-tetrahydrofuran (64 mL) was added dropwise a solution (36.9 mL) of 20% sodium ethoxide in ethanol under ice-cooling. After stirring at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Ester.Nitrile.Primary amine | Ester.Primary amine | c1ccccc1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccoc1 | TsOH.HO- | O1CCCC1.C(C)O | null | 12 | CCOC(=O)C(N)C(=O)OCC.Cc1ccc(S(=O)(=O)OC(=CC#N)c2ccco2)cc1>O1CCCC1.C(C)O>CCOC(=O)c1[nH]c(-c2ccco2)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95a54f43fb5e4d08b1d87ebe133e79b5 | CCOC(=O)c1[nH]c(-c2ccco2)cc1N.N=CN>>O=c1[nH]cnc2cc(-c3ccco3)[nH]c12 | NC1=C(NC(=C1)C=1OC=CC1)C(=O)OCC.C(C)(=O)O.C(=N)N>>O1C(=CC=C1)C1=CC=2N=CNC(C2N1)=O | CCO[C:2](=[O:1])[c:15]1[c:6]([NH2:5])[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][o:13]2)[nH:14]1.N[CH:4]=[NH:3]>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][o:13]3)[nH:14][c:15]12 | CCOC(=O)c1[nH]c(-c2ccco2)cc1N.N=CN | O=c1[nH]cnc2cc(-c3ccco3)[nH]c12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | cf2d93c547f6b79e1ff78c4c95ac2a9882be6c07ff6c3d38d4ab70f7d93654ab | 36efa24579e0043fdba8918e78f1d75cb4504837c08d344d01203f5fa64bfaef | O=c1[nH]cnc2cc(-c3ccco3)[nH]c12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[NH2;D1;+0:8].N-[CH;D2;+0:9]=[NH;D1;+0:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:10]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[c:7]2:[c:6]:[c:5]:[#7;a:4]:[c:3]:2:1 | 95.9 | [{"value": 95.9, "product": "O1C(=CC=C1)C1=CC=2N=CNC(C2N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 3-amino-5-(2-furyl)-1H-pyrrole-2-carboxylate (2.58 g) in ethanol (35 mL) was added formamidine acetate (1.83 g), and the mixture was heated under reflux for 18 hrs. After cooling to room temperature, the precipitated solid was collected by filtration, washed with ethanol, and dried under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | null | c1cc[nH]c1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccoc1 | HO- | C(C)O | null | null | CCOC(=O)c1[nH]c(-c2ccco2)cc1N.N=CN>C(C)O>O=c1[nH]cnc2cc(-c3ccco3)[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60364eed59cf42df9902b300bf8ffe2b | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccco3)[nH]c12>>Clc1ncnc2cc(-c3ccco3)[nH]c12 | O1C(=CC=C1)C1=CC=2N=CNC(C2N1)=O.P(=O)(Cl)(Cl)Cl>>ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2 | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][o:13]3)[nH:14][c:15]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][o:13]3)[nH:14][c:15]12 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccco3)[nH]c12 | Clc1ncnc2cc(-c3ccco3)[nH]c12 | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 990997bc80649f34ced0b0b8c9ec1b3d7f7bb4583bf26285f81a6c467d40b7b8 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1coc(-c2cc3ncncc3[nH]2)c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1 | 91.2 | [{"value": 91.2, "product": "ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 20 | MINUTE | A mixture of 6-(2-furyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-4-one (2.20 g) and phosphoryl chloride (10.7 g) was stirred at 100° C. for 20 min, dioxane (30 mL) was added, and the mixture was stirred at 100° C. for 3 hrs. After concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate was adde... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2ncncc2[nH]1 | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1.c1ccoc1 | HCl | O1CCOCC1 | 100 | 0.333333 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(-c3ccco3)[nH]c12>O1CCOCC1>Clc1ncnc2cc(-c3ccco3)[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12d14ab5c17b4725aa3770f42c1b9592 | Cc1ccc(Oc2ccc(N)cc2C)cn1.Clc1ncnc2cc(-c3ccco3)[nH]c12>>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2C)cn1 | C(O)([O-])=O.[Na+].ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C.CN1C(CCC1)=O>>O1C(=CC=C1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:26][c:27]2[CH3:28])[cH:29][n:30]1.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][o:23]3)[nH:24][c:25]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]4[cH:17][... | Cc1ccc(Oc2ccc(N)cc2C)cn1.Clc1ncnc2cc(-c3ccco3)[nH]c12 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2C)cn1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 57.3 | [{"value": 57.3, "product": "O1C(=CC=C1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (110 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (161 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccncc1.c1ccccc1.c1ncc2[nH]ccc2n1.c1ccoc1 | HCl | O | 140 | 2 | Cc1ccc(Oc2ccc(N)cc2C)cn1.Clc1ncnc2cc(-c3ccco3)[nH]c12>O>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cc40eed89874974a268b62f889db214 | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Fc1cccc(COc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2Cl)c1 | C(O)([O-])=O.[Na+].ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.CN1C(CCC1)=O>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2 | Cl[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][o:25]3)[nH:26][c:27]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:28][c:29]2[Cl:30])[cH:31]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][n... | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Fc1cccc(COc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2Cl)c1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 56 | [{"value": 56.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (110 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (189 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1.c1ccoc1 | HCl | O | 140 | 2 | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>O>Fc1cccc(COc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10af4feedcf24e3ba6816513f7f67db0 | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1>>Clc1cc(Nc2ncnc3cc(-c4ccco4)[nH]c23)ccc1OCc1ccccn1 | C(O)([O-])=O.[Na+].ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2.ClC=1C=C(N)C=CC1OCC1=NC=CC=C1.CN1C(CCC1)=O>>ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2 | Cl[c:6]1[n:7][cH:8][n:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][o:17]3)[nH:18][c:19]12.[Cl:1][c:2]1[cH:3][c:4]([NH2:5])[cH:20][cH:21][c:22]1[O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][o:17]4)[... | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1 | Clc1cc(Nc2ncnc3cc(-c4ccco4)[nH]c23)ccc1OCc1ccccn1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 4e9376aae532abc2c3c92cfa1996ed64a03a89441cc1d43f64dc118dec94ec57 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 46.6 | [{"value": 46.6, "product": "ClC=1C=C(C=CC1OCC1=NC=CC=C1)NC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (80 mg), 3-chloro-4-(pyridin-2-ylmethoxy)aniline (94 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccoc1.c1ccncc1 | HCl | O | 140 | 2 | Clc1ncnc2cc(-c3ccco3)[nH]c12.Nc1ccc(OCc2ccccn2)c(Cl)c1>O>Clc1cc(Nc2ncnc3cc(-c4ccco4)[nH]c23)ccc1OCc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f590447ac0b433096884f53a5ace055 | COC(=O)c1ccc(C(=O)CC#N)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>>COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1 | C(#N)CC(=O)C1=CC=C(C(=O)OC)C=C1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)N(CC)CC>>C(#N)C=C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=C(C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([CH2:10][C:11]#[N:12])=[O:13])[cH:24][cH:25]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[CH:10][C:11]#[N:12])[O:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]([CH3... | COC(=O)c1ccc(C(=O)CC#N)cc1.Cc1ccc(S(=O)(=O)Cl)cc1 | COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 9f8c97f001bd09a5896e1620aa92ed222c76fd261d4582b923c7f486d025fb40 | ad2bf1a301061ff4de8cacf445aa6c9f6615e0daaa746ef88ba96d39fc5112df | [CH]=C(OS(=O)(=O)c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]>>[N;D1;H0:7]#[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:10](-[O;H0;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[c:12](:[c:13]):[c:14] | 97.2 | [{"value": 97.2, "product": "C(#N)C=C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of methyl 4-(cyanoacetyl)benzoate (10.29 g), p-toluenesulfonyl chloride (11.58 g) and dichloromethane (110 mL) was added dropwise triethylamine (7.68 g) under ice-cooling. After stirring under ice-cooling for 2.5 hrs, the mixture was diluted with dichloromethane (100 mL), washed with water (150 mL), dried ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COC(=O)c1ccc(C(=O)CC#N)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ba17fa0a560407bb18f0473c2156def | CCOC(=O)C(N)C(=O)OCC.COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1>>CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1 | [O-]CC.[Na+].Cl.C(#N)C=C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=C(C(=O)OC)C=C1.Cl.NC(C(=O)OCC)C(=O)OCC>>NC1=C(NC(=C1)C1=CC=C(C=C1)C(=O)OCC)C(=O)OCC | O=C(O[CH2:2][CH3:1])[CH:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[NH2:20].Cc1ccc(S(=O)(=O)O[C:10]([c:9]2[cH:8][cH:7][c:6]([C:4]([O:3]C)=[O:5])[cH:22][cH:21]2)=[CH:11][C:12]#[N:13])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][c:12]([NH2:13])[c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[n... | CCOC(=O)C(N)C(=O)OCC.COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1 | CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1 | null | null | O1CCCC1.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 5a0500a596c38ffea4f79f3f3c03d502284d793b3d53693f26c30f1e46f66a23 | 43c496d8acff34bbf2f9380b19cdbc08333f79dbba42ae17715b324ab48e7f11 | c1ccc(-c2ccc[nH]2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c;H0;D3;+0:7](-[C;H0;D3;+0:8](-O-S(=O)(=O)-c2:c:c:c(-C):c:c:2)=[CH;D2;+0:9]-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]):[c:12]:[c:13]:1.O=C(-O-[CH2;D2;+0:14]-[C;D1;H3:15])-[CH;D3;+0:16](-[NH2;D1;+0:17])-[C:18](=[O;D1;H0:19])-[#8:20]-[C:21]>>[C:21]-[#8:20]-[C:18](=[O;D1;H0:1... | null | [] | null | null | null | null | To a suspension of methyl 4-(2-cyano-1-{[(4-methylphenyl)sulfonyl]oxy}vinyl)benzoate (17.5 g) and diethyl aminomalonate hydrochloride (10.36 g) in a mixed solvent of ethanol (165 mL)-tetrahydrofuran (80 mL) was added dropwise a solution (50 mL) of 20% sodium ethoxide in ethanol under ice-cooling. After stirring under i... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Ester.Ester.Nitrile.Primary amine | Ester.Ester.Primary amine | c1ccccc1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | TsOH.HO- | O1CCCC1.C(C)O | null | null | CCOC(=O)C(N)C(=O)OCC.COC(=O)c1ccc(C(=CC#N)OS(=O)(=O)c2ccc(C)cc2)cc1>O1CCCC1.C(C)O>CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23398c4f680f4fd6a53b3b6ec365b20c | CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1.N=CN>>CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1 | NC1=C(NC(=C1)C1=CC=C(C=C1)C(=O)OCC)C(=O)OCC.C(C)(=O)O.C(=N)N>>O=C1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2 | CCO[C:16](=[O:17])[c:18]1[c:12]([NH2:13])[cH:11][c:10](-[c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:21][cH:20]2)[nH:19]1.N[CH:14]=[NH:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][c:12]3[n:13][cH:14][nH:15][c:16](=[O:17])[c:18]3[nH:19]2)[cH:20][cH:21]1 | CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1.N=CN | CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | cf2d93c547f6b79e1ff78c4c95ac2a9882be6c07ff6c3d38d4ab70f7d93654ab | 36efa24579e0043fdba8918e78f1d75cb4504837c08d344d01203f5fa64bfaef | O=c1[nH]cnc2cc(-c3ccccc3)[nH]c12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[NH2;D1;+0:8].N-[CH;D2;+0:9]=[NH;D1;+0:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:10]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[c:7]2:[c:6]:[c:5]:[#7;a:4]:[c:3]:2:1 | 94.3 | [{"value": 94.3, "product": "O=C1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of ethyl 3-amino-5-[4-(ethoxycarbonyl)phenyl]-1H-pyrrole-2-carboxylate (3.36 g), formamidine acetate (1.74 g) and ethanol (60 mL) was heated under reflux for 15 hrs. After cooling to room temperature, the precipitated solid was collected by filtration, washed with ethanol, and dried under reduced pressure at ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | null | c1cc[nH]c1 | c1cc2ncncc2[nH]1 | c1ccccc1.c1cc2ncncc2[nH]1 | HO- | C(C)O | null | null | CCOC(=O)c1ccc(-c2cc(N)c(C(=O)OCC)[nH]2)cc1.N=CN>C(C)O>CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f73f8bea7c904e2399764dcdefce25f6 | CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl>>CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cl | O=C1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2.P(=O)(Cl)(Cl)Cl>>Cl.ClC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2 | O=[c:16]1[nH:15][cH:14][n:13][c:12]2[cH:11][c:10](-[c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:21][cH:20]3)[nH:19][c:18]21.O=P(Cl)([Cl:17])[Cl:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][c:12]3[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]3[nH:19]2)[cH:20][cH:21]1.[ClH:22] | CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cl | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 990997bc80649f34ced0b0b8c9ec1b3d7f7bb4583bf26285f81a6c467d40b7b8 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cc3ncncc3[nH]2)cc1 | Cl-P(=O)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:2:1.[ClH;D0;+0:2] | 94.2 | [{"value": 94.2, "product": "Cl.ClC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 1 | HOUR | A mixture of ethyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate (2.97 g) and phosphoryl chloride (16.45 g) was stirred at 110° C. for 1 hr, dioxane (10 mL) was added and the mixture was heated under reflux for 4 hrs. After concentration under reduced pressure, ethanol (30 mL) was added to the residue a... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2ncncc2[nH]1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1 | Other | O1CCOCC1 | 110 | 1 | CCOC(=O)c1ccc(-c2cc3nc[nH]c(=O)c3[nH]2)cc1.O=P(Cl)(Cl)Cl>O1CCOCC1>CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e690e0d37b5647b480ee3cba21bcd7dd | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cc1ccc(Oc2ccc(N)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1 | Cl.ClC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C.C(C)(C)N(CC)C(C)C.CN1C(CCC1)=O>>Cl.CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)O)C=C2 | CC[O:25][C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[cH:17][c:16]3[n:15][cH:14][n:13][c:12](Cl)[c:29]3[nH:28]2)[cH:27][cH:26]1)=[O:24].[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:30][c:31]2[CH3:32])[cH:33][n:34]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n... | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cc1ccc(Oc2ccc(N)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 521ad2e982ed77e44719df3f58454a49cf9127923079f040329e1018635dd0ce | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2cc3ncnc(Nc4ccc(Oc5cccnc5)cc4)c3[nH]2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:16]:[c:15](-[NH;D2;+0:14]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:1):... | 57.7 | [{"value": 57.7, "product": "Cl.CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 3 | HOUR | A mixture of ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride (1.297 g), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (1.00 g), diisopropylethylamine (0.834 g) and 1-methyl-2-pyrrolidinone (12.5 mL) was stirred at 140° C. for 3 hrs, poured into water (100 mL)-ethyl acetate (150 mL) and the prec... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccncc1.c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | HCl | O.C(C)(=O)OCC | 140 | 3 | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Cc1ccc(Oc2ccc(N)cc2C)cn1>O.C(C)(=O)OCC>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71723cd5d3864132b3a9cd98e9d39005 | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>O=C(O)c1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 | C(O)([O-])=O.[Na+].Cl.ClC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)OCC)C=C2.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.CN1C(CCC1)=O>>Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)O)C=C2 | CC[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[n:12][cH:13][n:14][c:15](Cl)[c:33]3[nH:34]2)[cH:35][cH:36]1.[NH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]2)[c:30]([Cl:31])[cH:32]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[n:1... | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | O=C(O)c1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 521ad2e982ed77e44719df3f58454a49cf9127923079f040329e1018635dd0ce | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(COc2ccc(Nc3ncnc4cc(-c5ccccc5)[nH]c34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[c:16]:[c:15](-[NH;D2;+0:14]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c:13]:2:1):... | 62 | [{"value": 62.0, "product": "Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 5 | HOUR | A mixture of ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride (517 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (462 mg) and 1-methyl-2-pyrrolidinone (8 mL) was stirred at 140° C. for 5 hrs, poured into water (40 mL), and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The pre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1 | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HCl | O | 140 | 5 | CCOC(=O)c1ccc(-c2cc3ncnc(Cl)c3[nH]2)cc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>O>O=C(O)c1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b3bfb9f6ba64d338b3412fe35f0ed62 | CI.Clc1ncnc2cc(-c3ccco3)[nH]c12>>Cn1c(-c2ccco2)cc2ncnc(Cl)c21 | O.ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2.C([O-])([O-])=O.[K+].[K+].CI>>ClC=1C2=C(N=CN1)C=C(N2C)C=2OC=CC2 | I[CH3:1].[nH:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][o:8]2)[cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]12>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][o:8]2)[cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]12 | CI.Clc1ncnc2cc(-c3ccco3)[nH]c12 | Cn1c(-c2ccco2)cc2ncnc(Cl)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 984dc1e2f23276e16434cf60f0728fced0721ac085a767b5a5daa33828d25b2d | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1coc(-c2cc3ncncc3[nH]2)c1 | I-[CH3;D1;+0:1].[#8;a:2]:[c:3]-[c:4]1:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](-[Cl;D1;H0:11]):[c:12]:2:[nH;D2;+0:13]:1>>[#8;a:2]:[c:3]-[c:4]1:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](-[Cl;D1;H0:11]):[c:12]:2:[n;H0;D3;+0:13]:1-[CH3;D1;+0:1] | 40.2 | [{"value": 40.2, "product": "ClC=1C2=C(N=CN1)C=C(N2C)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (220 mg) in N,N-dimethylformamide (2.5 mL) were added potassium carbonate (139 mg) and methyl iodide (0.25 mL) and the mixture was stirred at room temperature for 8 hrs. The mixture was poured into water (30 mL) and extracted with ethyl acetate (30 mL×3)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2[nH]ccc2n1 | c1cc2ncncc2[nH]1 | c1ccoc1.c1cc2ncncc2[nH]1 | HI | CN(C=O)C | null | 8 | CI.Clc1ncnc2cc(-c3ccco3)[nH]c12>CN(C=O)C>Cn1c(-c2ccco2)cc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c52e7509444a496d9253b6abe0ab4828 | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1c(-c2ccco2)cc2ncnc(Cl)c21>>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)n(C)c34)cc2C)cn1 | C(O)([O-])=O.[Na+].ClC=1C2=C(N=CN1)C=C(N2C)C=2OC=CC2.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C.CN1C(CCC1)=O>>O1C(=CC=C1)C1=CC=2N=CN=C(C2N1C)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:27][c:28]2[CH3:29])[cH:30][n:31]1.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][o:23]3)[n:24]([CH3:25])[c:26]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][n:15][c:16]... | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1c(-c2ccco2)cc2ncnc(Cl)c21 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)n(C)c34)cc2C)cn1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | a761a23478bcca0adfe0c4dd4341ad165c5bf801aa5c397f8a3fb7ad8077557d | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 64.8 | [{"value": 64.8, "product": "O1C(=CC=C1)C1=CC=2N=CN=C(C2N1C)NC1=CC(=C(C=C1)OC=1C=NC(=CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 3.5 | HOUR | A mixture of 4-chloro-6-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (92 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (102 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 3.5 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1 | c1ccncc1.c1ccccc1.c1cc2ncncc2[nH]1.c1ccoc1 | HCl | O | 140 | 3.5 | Cc1ccc(Oc2ccc(N)cc2C)cn1.Cn1c(-c2ccco2)cc2ncnc(Cl)c21>O>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)n(C)c34)cc2C)cn1 |
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