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-03ba810b7f464a06b5d8787af2e8b64e | ord-bf261ed710fe4fe4af6a038ad9a8bcf1 | CCOC(=O)/N=N/C(=O)OCC.O=C(c1ccccc1)n1c(=O)cc[nH]c1=O.OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1>>N.O=C(c1ccccc1)n1c(=O)ccn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | FC(C1=CC=C(C=C1)[C@]12CN(C[C@@H]2C1)CCCO)(F)F.C1(=CC=CC=C1)C(=O)N1C(NC=CC1=O)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CCOC(=O)/N=N/C(=O)OCC>>N.C1(=CC=CC=C1)C(=O)N1C(N(C=CC1=O)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O | CCOC(=O)/N=[N:1]/C(=O)OCC.[O:2]=[C:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[c:11](=[O:12])[cH:13][cH:14][nH:15][c:35]1=[O:36].O[CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][C@@H:21]2[CH2:22][C@:23]2([c:24]2[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]2)[CH2:34]1>>[NH3:1].[O:2]=[C:3]([c:4]1[cH:5][cH... | CCOC(=O)/N=N/C(=O)OCC.O=C(c1ccccc1)n1c(=O)cc[nH]c1=O.OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1 | N.O=C(c1ccccc1)n1c(=O)ccn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c592a6d3815abe1b0fcd9119a843c8497601ce4c2b7e7b08cd7e44e6368c60c6 | d2bf6c01b3df7e65bad3bc3312b3ebd72ceecc017af88ca43f5931c08c331132 | O=C(c1ccccc1)n1c(=O)ccn(CCCN2C[C@@H]3C[C@]3(c3ccccc3)C2)c1=O | C-C-O-C(=O)/N=[N;H0;D2;+0:1]/C(=O)-O-C-C.O-[CH2;D2;+0:2]-[C:3]-[C:4].[O;D1;H0:5]=[C:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[#7;a:7](-[C:6]=[O;D1;H0:5]):[c:12]:1=[O;D1;H0:13].[NH3;D0;+0:1] | null | [] | null | null | null | null | To a solution of 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol (Prep5, 51 mg), 3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (39 mg, prepared according to the procedure reported in J. Chem. Soc., Perkin Trans. 1, 2827 (1998)) and PPh3 (140 mg) in dry dioxane at 110° C., DEAD (40% solu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Primary alcohol | null | c1ccncn1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1[NH]C[C@H]2C[C@@H]12.c1ccccc1 | HO- | O1CCOCC1 | null | null | CCOC(=O)/N=N/C(=O)OCC.O=C(c1ccccc1)n1c(=O)cc[nH]c1=O.OCCCN1C[C@@H]2C[C@]2(c2ccc(C(F)(F)F)cc2)C1>O1CCOCC1>N.O=C(c1ccccc1)n1c(=O)ccn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0f56a0657d244ad79378abcbc156cbfa | C[Si](C)(C)Oc1ncc(F)c(O[Si](C)(C)C)n1.ClCCCBr>>O=c1[nH]c(=O)n(CCCCl)cc1F | BrCCCCl.II.[OH-].[Na+].FC=1C(=NC(=NC1)O[Si](C)(C)C)O[Si](C)(C)C>>ClCCCN1C(NC(C(=C1)F)=O)=O | C[Si](C)(C)[O:1][c:2]1[n:3][c:4]([O:5][Si](C)(C)C)[n:6][cH:11][c:12]1[F:13].Br[CH2:7][CH2:8][CH2:9][Cl:10]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]1[F:13] | C[Si](C)(C)Oc1ncc(F)c(O[Si](C)(C)C)n1.ClCCCBr | O=c1[nH]c(=O)n(CCCCl)cc1F | null | null | O.ClCCCl | Acylation | OtherReaction | ef7e38e85ec505c877e8ac38067aa7be9541ea3721892ea74eeed95e80f80e36 | 56e489388a260cefd141e453e6b7d032ad8e0761b73347385ac6efe69f6c5003 | O=c1cc[nH]c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-[Si](-C)(-C)-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[O;H0;D2;+0:8]-[Si](-C)(-C)-C):[n;H0;D2;+0:9]:[c:10]:[c:11]:1-[F;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:5](=[O;H0;D1;+0:4]):[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;H0... | null | [] | null | null | null | null | A mixture of 5-fluoro-2,4-bis[(trimethylsilyl)oxy]pyrimidine (1 g, commercially available from Lancaster), 1-bromo-3-chloropropane (0.44 mL) and I2 (10 mg) in 1,2-dichloroethane (10 mL) was heated to reflux for 30 h. Then the reaction mixture was treated with water and the pH was brought to 7 using aqueous 6N NaOH solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Silyl protective group.Silyl protective group | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | O.ClCCCl | null | null | C[Si](C)(C)Oc1ncc(F)c(O[Si](C)(C)C)n1.ClCCCBr>O.ClCCCl>O=c1[nH]c(=O)n(CCCCl)cc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-37721b0f049b466395e868dac77cf5c5 | CC(Cl)CCCBr.Cc1c[nH]c(=O)[nH]c1=O>>Cc1cn(CCCC(C)Cl)c(=O)[nH]c1=O | O.CC=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCC(C)Cl>>ClC(CCCN1C(NC(C(=C1)C)=O)=O)C | Br[CH2:5][CH2:6][CH2:7][CH:8]([CH3:9])[Cl:10].[CH3:1][c:2]1[cH:3][nH:4][c:11](=[O:12])[nH:13][c:14]1=[O:15]>>[CH3:1][c:2]1[cH:3][n:4]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:9])[Cl:10])[c:11](=[O:12])[nH:13][c:14]1=[O:15] | CC(Cl)CCCBr.Cc1c[nH]c(=O)[nH]c1=O | Cc1cn(CCCC(C)Cl)c(=O)[nH]c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1cc[nH]c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | A mixture of 5-methyl-2,4(1H,3H)-pyrimidinedione (thimine, 500 mg) and K2CO3 (548 g) in dry DMF (15 mL) was stirred for 1 hour at room temperature. 1-bromo-4-chloropentane (0.548 mL) was then added and the mixture was stirred at room temperature for 4 hours. Water was then added and the resulting mixture was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | CN(C)C=O | null | 1 | CC(Cl)CCCBr.Cc1c[nH]c(=O)[nH]c1=O>CN(C)C=O>Cc1cn(CCCC(C)Cl)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b5c69ff97ec84d499f849aef7bdff788 | ClCCCBr.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1>>FC(F)(F)c1ccc([C@]23C[C@H]2CN(CCCCl)C3)cc1 | FC(C1=CC=C(C=C1)[C@]12CNC[C@@H]2C1)(F)F.BrCCCCl>>ClCCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F | Br[CH2:14][CH2:15][CH2:16][Cl:17].[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([C@:9]23[CH2:10][C@H:11]2[CH2:12][NH:13][CH2:18]3)[cH:19][cH:20]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([C@:9]23[CH2:10][C@H:11]2[CH2:12][N:13]([CH2:14][CH2:15][CH2:16][Cl:17])[CH2:18]3)[cH:19][cH:20]1 | ClCCCBr.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1 | FC(F)(F)c1ccc([C@]23C[C@H]2CN(CCCCl)C3)cc1 | null | null | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d146f4fec15b76edef859aca9895175d902089a964e188856a16a2c19aad64e8 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc([C@@]23CNC[C@@H]2C3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[C:8]-[C:7]-1 | null | [] | null | null | null | null | To a solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (P4, 1.00 g) in dry THF (5 mL), DIPEA (2.4 mL) and 1-bromo-3-chloropropane (3.7 mL) were added and the resulting mixture was heated at reflux for 3 hours. After cooling at room temperature it was diluted with EtOAc (30 mL) washed twice wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1NC[C@@H]2C[C@@H]12 | C1[NH]C[C@@H]2C[C@@H]12 | c1ccccc1.C1[NH]C[C@@H]2C[C@@H]12 | HBr | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(=O)C | null | null | ClCCCBr.FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(=O)C>FC(F)(F)c1ccc([C@]23C[C@H]2CN(CCCCl)C3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8a8197255c98431ca6db0b3bf5cce1ee | ClCCCBr.O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1>>O=c1[nH]c(=O)n(CCCCl)cc1-c1ccccc1 | BrCCCCl.O.C1(=CC=CC=C1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClCCCN1C(NC(C(=C1)C1=CC=CC=C1)=O)=O | Br[CH2:7][CH2:8][CH2:9][Cl:10].[O:1]=[c:2]1[nH:3][c:4](=[O:5])[nH:6][cH:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | ClCCCBr.O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1 | O=c1[nH]c(=O)n(CCCCl)cc1-c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | null | null | 20 | HOUR | A mixture of 5-phenyl-2,4(1H,3H)-pyrimidinedione (527 mg, commercially available from Akos) and K2CO3 (386 mg) in dry DMF (10 mL) was stirred for 1 hour at room temperature. 1-Bromo-3-chloropropane (0.28 mL) was added and the mixture was stirred at room temperature for 20 hours. One more portion of 1-bromo-3-chloroprop... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | null | 20 | ClCCCBr.O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1>CN(C)C=O>O=c1[nH]c(=O)n(CCCCl)cc1-c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1a75229b12604ed7ac0796073c57a14f | ClCCCBr.O=c1[nH]cc(N2CCCC2)c(=O)[nH]1>>O=c1[nH]c(=O)n(CCCCl)cc1N1CCCC1 | O.N1(CCCC1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClCCCN1C(NC(C(=C1)N1CCCC1)=O)=O | Br[CH2:7][CH2:8][CH2:9][Cl:10].[O:1]=[c:2]1[nH:3][c:4](=[O:5])[nH:6][cH:11][c:12]1[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]1[N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1 | ClCCCBr.O=c1[nH]cc(N2CCCC2)c(=O)[nH]1 | O=c1[nH]c(=O)n(CCCCl)cc1N1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(N2CCCC2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | null | null | 20 | HOUR | A mixture of 5-(1-pyrrolidinyl)-2,4(1H,3H)-pyrimidinedione (507 mg, commercially available from Interchim Intermediates) and K2CO3 (386 mg) in dry DMF (10 mL) was stirred for 1 hour at room temperature. 1-Bromo-3-chloropropane (0.28 mL) was added and the mixture was stirred at room temperature for 20 hours. Water was a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CC[NH]C1 | HBr | CN(C)C=O | null | 20 | ClCCCBr.O=c1[nH]cc(N2CCCC2)c(=O)[nH]1>CN(C)C=O>O=c1[nH]c(=O)n(CCCCl)cc1N1CCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ea365151b023425aaee1271b58ac08e1 | CC(C)(C)[Si](C)(C)OCCCBr.O=c1[nH]cc(C(F)(F)F)c(=O)[nH]1>>CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | [H-].[Na+].FC(C=1C(NC(NC1)=O)=O)(F)F.BrCCCO[Si](C)(C)C(C)(C)C>>C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O)(C)C | 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][c:14]([C:15]([F:16])([F:17])[F:18])[c:19](=[O:20])[nH:21][c:22]1=[O:23]>>[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][c:14]([C:15]([F:16])([F:17])[F:18])[c:19](=[O:20]... | CC(C)(C)[Si](C)(C)OCCCBr.O=c1[nH]cc(C(F)(F)F)c(=O)[nH]1 | CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1cc[nH]c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 37.1 | [{"value": 37.0, "product": "C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.1, "product": "C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | To a suspension of 50% NaH (0.42 g, 8.7 mmol) in DMF (5 mL), a solution of 5-trifluoromethyl-1H-pyrimidine-2,4-dione (1.2 g, 6.66 mmol) was added drop wise maintaining the temperature at 0° C. The mixture was then heated at 100° C. for 1 hour. After cooling to room temperature, (3-bromo-propoxy)-tert-butyl-dimethyl-sil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | CN(C)C=O | 0 | 8 | CC(C)(C)[Si](C)(C)OCCCBr.O=c1[nH]cc(C(F)(F)F)c(=O)[nH]1>CN(C)C=O>CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ccb073e46e534ab58490533d67947800 | CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O>>O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F | C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O)(C)C.C(=O)(C(F)(F)F)O>>OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O | CC(C)(C)[Si](C)(C)[O:10][CH2:9][CH2:8][CH2:7][n:6]1[c:4](=[O:5])[nH:3][c:2](=[O:1])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][OH:10])[cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F | null | null | C(Cl)Cl | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=c1cc[nH]c(=O)[nH]1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 57.7 | [{"value": 57.0, "product": "OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.7, "product": "OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-trifluoromethyl-1H-pyrimidine-2, 4-dione (Prep 19, 0.86 g, 2.4 mmol) in DCM (10 mL) was cooled at 0° C. and then TFA (2.8 mL, 36 mmol) was added. The mixture was stirred for 1 hour at room temperature and then the solvent was evaporated. The crude was purifi... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1cncnc1 | Other | C(Cl)Cl | null | 1 | CC(C)(C)[Si](C)(C)OCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O>C(Cl)Cl>O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7803cddafcb04961b30e4533461f82af | O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F>>O=CCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | OCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.CCOCC>>FC(C=1C(NC(N(C1)CCC=O)=O)=O)(F)F | [OH:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12](=[O:13])[nH:14][c:15]1=[O:16]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12](=[O:13])[nH:14][c:15]1=[O:16] | O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F | O=CCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | null | null | C1CCOC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1cc[nH]c(=O)[nH]1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 68 | [{"value": 68.0, "product": "FC(C=1C(NC(N(C1)CCC=O)=O)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.4, "product": "FC(C=1C(NC(N(C1)CCC=O)=O)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | 1-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep20, 100 mg, 0.42 mmol) was dissolved in dry THF (5 mL), the solution was then cooled to 0° C. and Dess-Martin periodinane (300 mg, 0.71 mmol) was added. The mixture was stirred at 0° C. for 1.5 hours. Et2O was added and the mixture washed with aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1 | null | C1CCOC1 | 0 | 1.5 | O=c1[nH]c(=O)n(CCCO)cc1C(F)(F)F>C1CCOC1>O=CCCn1cc(C(F)(F)F)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fe9abdc192c54b518602509531500c56 | CC(C)(C)[Si](C)(C)OCCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O>>O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F | C(C)(C)(C)[Si](OCCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O)(C)C.C(=O)(C(F)(F)F)O>>OCCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O | CC(C)(C)[Si](C)(C)[O:11][CH2:10][CH2:9][CH2:8][CH2:7][n:6]1[c:4](=[O:5])[nH:3][c:2](=[O:1])[c:13]([C:14]([F:15])([F:16])[F:17])[cH:12]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[cH:12][c:13]1[C:14]([F:15])([F:16])[F:17] | CC(C)(C)[Si](C)(C)OCCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F | null | null | C(Cl)Cl | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=c1cc[nH]c(=O)[nH]1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 74 | [{"value": 74.0, "product": "OCCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.7, "product": "OCCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep22, 260 mg, 0.71 mmol) in DCM (15 mL) was cooled at 0° C. and then TFA (820 μl, 1.1 mmol) was added. The mixture was stirred for 1 hour at room temperature and the solvent was evaporated. The crude was purified by ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1cncnc1 | Other | C(Cl)Cl | null | 1 | CC(C)(C)[Si](C)(C)OCCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O>C(Cl)Cl>O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2d9ddf4e5bc948ea8390a84b8afb5556 | O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F>>O=CCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | OCCCCN1C(NC(C(=C1)C(F)(F)F)=O)=O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.CCOCC>>FC(C=1C(NC(N(C1)CCCC=O)=O)=O)(F)F | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13](=[O:14])[nH:15][c:16]1=[O:17]>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13](=[O:14])[nH:15][c:16]1=[O:17] | O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F | O=CCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O | null | null | C1CCOC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1cc[nH]c(=O)[nH]1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 51.7 | [{"value": 50.0, "product": "FC(C=1C(NC(N(C1)CCCC=O)=O)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.7, "product": "FC(C=1C(NC(N(C1)CCCC=O)=O)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | 1-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep 23, 44 mg, 0.17 mmol) was dissolved in dry THF (5 mL), the solution was cooled to 0° C. and Dess-Martin periodinane (127 mg, 0.28 mmol) was added. The mixture was stirred at 0° C. for 1.5 hours. Et2O was added and the solution washed with aqueous satur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1 | null | C1CCOC1 | 0 | 1.5 | O=c1[nH]c(=O)n(CCCCO)cc1C(F)(F)F>C1CCOC1>O=CCCCn1cc(C(F)(F)F)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6a27ead10db740a4ac7fefbba65f9c12 | CC(C)(C)Oc1ncc(B(O)O)c(OC(C)(C)C)n1.Cc1ccsc1Br>>Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C | C(C)(C)(C)OC1=NC=C(C(=N1)OC(C)(C)C)B(O)O.BrC=1SC=CC1C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(C)(C)OC1=NC=C(C(=N1)OC(C)(C)C)C=1SC=CC1C | OB(O)[c:7]1[cH:8][n:9][c:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Br[c:6]1[c:2]([CH3:1])[cH:3][cH:4][s:5]1>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9][c:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[O:18][C:19]([CH3:20])([CH3:21])[CH3:22... | CC(C)(C)Oc1ncc(B(O)O)c(OC(C)(C)C)n1.Cc1ccsc1Br | Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | fa60150a535c82f529b2e4e94a1f9aff1bdb8bdc0c7192900fea8f6f91a5e129 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1csc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C;D1;H3:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]-[C:14](-[C;D... | 32 | [{"value": 32.0, "product": "C(C)(C)(C)OC1=NC=C(C(=N1)OC(C)(C)C)C=1SC=CC1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.3, "product": "C(C)(C)(C)OC1=NC=C(C(=N1)OC(C)(C)C)C=1SC=CC1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Di-tert-butoxy-pyrimidine-5-boronic acid (500 mg, 1.75 mmol) was dissolved in n-PrOH (5 mL) and then 2-bromo-3-methylthiophene (236 μl, 2.1 mmol), Na2CO3 (556 mg, 5.25 mmol), PPh3 (133 mg, 0.52 mmol) and Pd(OAc)2 (40 mg, 0.17 mmol) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evap... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccsc1 | c1ccsc1.c1cncnc1 | c1ccsc1.c1cncnc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | CC(C)(C)Oc1ncc(B(O)O)c(OC(C)(C)C)n1.Cc1ccsc1Br>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-40a4ef48518c4ccc87e1f68997792b69 | Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C>>Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O | C(C)(C)(C)OC1=NC=C(C(=N1)OC(C)(C)C)C=1SC=CC1C>>CC1=C(SC=C1)C=1C(NC(NC1)=O)=O | CC(C)(C)[O:11][c:10]1[n:9][cH:8][c:7](-[c:6]2[c:2]([CH3:1])[cH:3][cH:4][s:5]2)[c:13]([O:14]C(C)(C)C)[n:12]1>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][nH:9][c:10](=[O:11])[nH:12][c:13]1=[O:14] | Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C | Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C(-C)(-C)-C):[c:6](-[c:7]:[#16;a:8]):[c:9]:[n;H0;D2;+0:10]:1>>[#16;a:8]:[c:7]-[c:6]1:[c:9]:[nH;D2;+0:10]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:3]:[c;H0;D3;+0:4]:1=[O;H0;D1;+0:5] | 101.6 | [{"value": 101.6, "product": "CC1=C(SC=C1)C=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2,4-di-tert-butoxy-5-(3-methyl-thiophen-2-yl)-pyrimidine (Prep 25, 165 mg, 0.52 mmol) in dioxane (5 mL) 4N HClaq in dioxane (1 mL) was added at 0° C. After stirring for 8 hours, the mixture was evaporated to give 110 mg of the title compound as white solid (quantitative yield)
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1ccsc1.c1cncnc1 | Other | O1CCOCC1 | null | 8 | Cc1ccsc1-c1cnc(OC(C)(C)C)nc1OC(C)(C)C>O1CCOCC1>Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-02bf8d507037412cb69175d867be4cb6 | CC(C)(C)[Si](C)(C)OCCCBr.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O>>Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O | BrCCCO[Si](C)(C)C(C)(C)C.CC1=C(SC=C1)C=1C(NC(NC1)=O)=O.[H-].[Na+]>>C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C | Br[CH2:10][CH2:11][CH2:12][O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[CH3:20].[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][nH:9][c:21](=[O:22])[nH:23][c:24]1=[O:25]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3... | CC(C)(C)[Si](C)(C)OCCCBr.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O | Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 37 | [{"value": 37.0, "product": "C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | To a suspension of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep26, 110 mg, 0.52 mmol) in dry DMF (10 mL), 60% NaH (31 mg, 0.78 mmol) was added. The mixture was then heated at 100° C. for 1 hour. (3-bromo-propoxy)-tert-butyl-dimethyl-silane (180 μl, 0.7 mmol) was then added at room temperature and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1ccsc1.c1cncnc1 | HBr | CN(C)C=O | 100 | 8 | CC(C)(C)[Si](C)(C)OCCCBr.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O>CN(C)C=O>Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-61cb07fdf24b499da184216c1f1a6b39 | Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O>>Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O | C(C)(C)(C)[Si](OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C.Cl>>OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O | CC(C)(C)[Si](C)(C)[O:13][CH2:12][CH2:11][CH2:10][n:9]1[cH:8][c:7](-[c:6]2[c:2]([CH3:1])[cH:3][cH:4][s:5]2)[c:17](=[O:18])[nH:16][c:14]1=[O:15]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][OH:13])[c:14](=[O:15])[nH:16][c:17]1=[O:18] | Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O | Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O | null | null | O1CCOCC1 | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 72 | [{"value": 72.0, "product": "OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 27, 73 mg, 0.2 mmol) in dioxane (8 mL) was cooled at 0° C. and then 4N HCl in dioxane (0.5 mL) was added. The mixture was stirred for 1 hour at room temperature and then the solvent was evaporated. The c... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccsc1.c1cncnc1 | Other | O1CCOCC1 | null | 1 | Cc1ccsc1-c1cn(CCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O>O1CCOCC1>Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6cb627a6ee604040bc5f5bdbf9aeff00 | Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O>>Cc1ccsc1-c1cn(CCC=O)c(=O)[nH]c1=O | OCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.C(C)(=O)OCC>>CC1=C(SC=C1)C=1C(NC(N(C1)CCC=O)=O)=O | [CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][OH:13])[c:14](=[O:15])[nH:16][c:17]1=[O:18]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH:12]=[O:13])[c:14](=[O:15])[nH:16][c:17]1=[O:18] | Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O | Cc1ccsc1-c1cn(CCC=O)c(=O)[nH]c1=O | null | null | C1CCOC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": "CC1=C(SC=C1)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.5, "product": "CC1=C(SC=C1)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | 1-(3-Hydroxy-propyl)-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 28.36 mg, 0.13 mmol) was dissolved in dry THF (5 mL), the solution was cooled to 0° C. and then Dess-Martin periodinane (97 mg, 0.22 mmol) was added under nitrogen. The mixture was stirred at room temperature for 1.5 hours. Ethyl acetate was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccsc1.c1cncnc1 | null | C1CCOC1 | 0 | 1.5 | Cc1ccsc1-c1cn(CCCO)c(=O)[nH]c1=O>C1CCOC1>Cc1ccsc1-c1cn(CCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f8276ed10f254d9d97d0a20aa58f09dd | CC(C)(C)[Si](C)(C)OCCCCI.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O>>Cc1ccsc1-c1cn(CCCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O | O.ICCCCO[Si](C)(C)C(C)(C)C.CC1=C(SC=C1)C=1C(NC(NC1)=O)=O.[H-].[Na+]>>C(C)(C)(C)[Si](OCCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C | I[CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21].[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][nH:9][c:22](=[O:23])[nH:24][c:25]1=[O:26]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([CH3:16])([CH3:17])[C:18]... | CC(C)(C)[Si](C)(C)OCCCCI.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O | Cc1ccsc1-c1cn(CCCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 23.2 | [{"value": 23.0, "product": "C(C)(C)(C)[Si](OCCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.2, "product": "C(C)(C)(C)[Si](OCCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 24 | HOUR | To a solution of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 26, 250 mg, 1.2 mmol) in DMF (10 mL), 60% NaH (58 mg, 1.44 mmol) was added portionwise. The reaction was then heated to 70° C. and this temperature was maintained for 1.5 hour. After cooling to room temperature, (4-iodo-butoxy)-tert-butyl-dimethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1ccsc1.c1cncnc1 | HI | CN(C)C=O | 70 | 24 | CC(C)(C)[Si](C)(C)OCCCCI.Cc1ccsc1-c1c[nH]c(=O)[nH]c1=O>CN(C)C=O>Cc1ccsc1-c1cn(CCCCO[Si](C)(C)C(C)(C)C)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-baa49772bb874fcea3044e6892cedd97 | Cc1ccsc1-c1cn(CCCCO)c(=O)[nH]c1=O>>Cc1ccsc1-c1cn(CCCC=O)c(=O)[nH]c1=O | OCCCCN1C(NC(C(=C1)C=1SC=CC1C)=O)=O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.C(C)(=O)OCC>>CC1=C(SC=C1)C=1C(NC(N(C1)CCCC=O)=O)=O | [CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19] | Cc1ccsc1-c1cn(CCCCO)c(=O)[nH]c1=O | Cc1ccsc1-c1cn(CCCC=O)c(=O)[nH]c1=O | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=c1[nH]cc(-c2cccs2)c(=O)[nH]1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 98 | [{"value": 98.0, "product": "CC1=C(SC=C1)C=1C(NC(N(C1)CCCC=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "CC1=C(SC=C1)C=1C(NC(N(C1)CCCC=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | 1-(4-Hydroxy-butyl)-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 31, 30 mg, 0.11 mmol) was dissolved in dry DCM (2 mL), the solution was cooled to 0° C. and Dess-Martin periodinane (113 mg, 0.26 mmol) was added portionwise under nitrogen. The mixture was stirred at room temperature for 1.5 hours. Ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccsc1.c1cncnc1 | null | C(Cl)Cl | 0 | 1.5 | Cc1ccsc1-c1cn(CCCCO)c(=O)[nH]c1=O>C(Cl)Cl>Cc1ccsc1-c1cn(CCCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-62cee4579b5c4dd7a0d29b59c51a8f86 | CCOC(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC>>CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | C(C)OC(NC(C(=COCC)C#N)=O)=O.C(C)OC(CCN)OCC>>C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)OCC | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][NH2:7])[O:17][CH2:18][CH3:19].CCO[CH:8]=[C:9]([C:10]#[N:11])[C:12](=[O:13])[NH:14][C:15](OCC)=[O:16]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][n:7]1[cH:8][c:9]([C:10]#[N:11])[c:12](=[O:13])[nH:14][c:15]1=[O:16])[O:17][CH2:18][CH3:19] | CCOC(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC | CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 294eb494ecaef8e3ca4dca852d6073988c8299ff97a84c68a5ea24695be2d73f | 4a855cedd5facbdcee72b4835f1264911b7b12388e618f5335fca61a604f6099 | O=c1cc[nH]c(=O)[nH]1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3]#[N;D1;H0:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-C-C.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[n;H0;D3;+0:12]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3]#[N;D1;H0:4]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c;H0;D3;+0:8]:1=[O;D1;H0:9] | 92.2 | [{"value": 91.0, "product": "C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (2-Cyano-3-ethoxy-acryloyl)-carbamic acid ethyl ester (Prep 33, 300 mg, 1.42 mmol) was suspended in water (20 mL); 3,3-diethoxypropylamine (460 μl, 2.84 mmol) was added and the mixture warmed at 80° C. for 10 minutes. The reaction mixture was lyophilized and the residue was purified by flash chromatography with petrole... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Unsubstituted dicarboximide.Primary amine | null | null | c1cncnc1 | c1cncnc1 | HO- | O | 80 | null | CCOC(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC>O>CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ee4295b20e334f398cc183b168edb499 | CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC>>N#Cc1cn(CCC=O)c(=O)[nH]c1=O | C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)OCC>>O=C1N(C=C(C(N1)=O)C#N)CCC=O | CCO[CH:8]([CH2:7][CH2:6][n:5]1[cH:4][c:3]([C:2]#[N:1])[c:13](=[O:14])[nH:12][c:10]1=[O:11])[O:9]CC>>[N:1]#[C:2][c:3]1[cH:4][n:5]([CH2:6][CH2:7][CH:8]=[O:9])[c:10](=[O:11])[nH:12][c:13]1=[O:14] | CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | N#Cc1cn(CCC=O)c(=O)[nH]c1=O | null | null | O1CCOCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1cc[nH]c(=O)[nH]1 | C-C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 130.7 | [{"value": 130.7, "product": "O=C1N(C=C(C(N1)=O)C#N)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-(3,3-diethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (Prep 34, 50 mg, 0.21 mmol) was dissolved in dioxane (5 mL) and 1N HClaq (500 μl) was added. The mixture was warmed at 60° C. for 15 minutes. The solvents were evaporated and the residue submitted to liophilization to give 53 mg of the title... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1 | HO- | O1CCOCC1 | 60 | null | CCOC(CCn1cc(C#N)c(=O)[nH]c1=O)OCC>O1CCOCC1>N#Cc1cn(CCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-09104cf4b34540c9b46bfd2433b383d8 | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1>>O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | IC=1C(NC(NC1)=O)=O.C(C1=CC=CC=C1)(=O)Cl.O>>C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[nH:9]1[c:10](=[O:11])[nH:12][cH:13][c:14]([I:15])[c:16]1=[O:17]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[nH:12][cH:13][c:14]([I:15])[c:16]1=[O:17] | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1 | O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | null | null | N1=CC=CC=C1 | Acylation | N-alkylation of secondary amines with alkyl halides | 424d6b217c72b1bfc74a70456602e1889d454da2579c9467b12c0e5157dbc176 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:1>>[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 5-iodouracil (commercially available from Aldrich, 2 g, 8.4 mmol) in dry pyridine (20 mL) was added dropwise to a solution of benzoyl chloride (3.5 g, 25.3 mmol) in pyridine (10 mL). The mixture was stirred at room temperature for 3 hours. Water (70 mL) was added and the product extracted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | N1=CC=CC=C1 | null | 3 | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1>N1=CC=CC=C1>O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dbe5faee50cd40d8b78bce49cf576f06 | COC(CCBr)OC.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>>COC(CCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O)OC | O.C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCC(OC)OC)=O | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:23][CH3:24].[nH:6]1[cH:7][c:8]([I:9])[c:10](=[O:11])[n:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1=[O:22]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8]([I:9])[c:10](=[O:11])[n:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1=[... | COC(CCBr)OC.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | COC(CCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1=[O;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6](-[C:5]=[O;D1;H0:4]):[c:11]:1=[O;D1;H0:12] | 91.8 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCC(OC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCC(OC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep 36, 2.1 g, 6.13 mmol), K2CO3 (846 mg, 6.13 mmol) and 3-bromo-1,1dimethoxy-propane (1 mL, 7.4 mmol) were dissolved in dry DMF under Nitrogen (8 mL). After stirring the reaction at room temperature for 48 h, water was added and the product extracted with diethylether. The or... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | null | null | COC(CCBr)OC.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>CN(C)C=O>COC(CCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-74726e650c6f46b7980399e0dc3cc6f7 | FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCC=O)=O.FC(C1=CC=C(C=C1)[C@]12CNC[C@@H]2C1)(F)F.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O | [NH:19]1[CH2:20][C@@H:21]2[CH2:22][C@:23]2([c:24]2[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]2)[CH2:34]1.O=[CH:18][CH2:17][CH2:16][n:15]1[cH:14][c:12]([I:13])[c:10](=[O:11])[n:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[c:35]1=[O:36]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:... | FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | null | null | ClCCl.O | Heteroatom Alkylation and Arylation | reductive amination | 7582a768b784ee3da33b6fe02c4a5c31bfb420d090c507a0e271b338a126f7e5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(c1ccccc1)n1c(=O)ccn(CCCN2C[C@@H]3C[C@]3(c3ccccc3)C2)c1=O | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | 84.9 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 0 | CELSIUS | 1 | HOUR | To a solution of 3-(3-benzoyl-5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde (Prep 38, 700 mg, 1.7 mmol) in dichloromethane (20 mL), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep 4, 399 mg, 1.7 mmol), AcOH (158 mg, 2.5 mmol) and NaBH(AcO)3 (410 mg, 1.9 mmol) were added at 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1NC[C@H]2C[C@@H]12 | C1[NH]C[C@H]2C[C@@H]12 | c1ccccc1.c1cncnc1.C1[NH]C[C@H]2C[C@@H]12.c1ccccc1 | Other | ClCCl.O | 0 | 1 | FC(F)(F)c1ccc([C@@]23CNC[C@@H]2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>ClCCl.O>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e8ff280b1b2d40039c2c5cf79d7bd198 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O>>O=c1[nH]c(=O)n(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)cc1I | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O>>IC=1C(NC(N(C1)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O)=O | O=C(c1ccccc1)[n:3]1[c:2](=[O:1])[c:27]([I:28])[cH:26][n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][C@@H:12]3[CH2:13][C@:14]3([c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[CH2:25]2)[c:4]1=[O:5]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][C@@H:12]3[CH2:13][C@:14]3([... | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O | O=c1[nH]c(=O)n(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)cc1I | null | null | CO.N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1ccn(CCCN2C[C@@H]3C[C@]3(c3ccccc3)C2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:7]-[#7;a:6]1:[c:5]:[c:4]:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:8]:1=[O;D1;H0:9] | 74 | [{"value": 74.0, "product": "IC=1C(NC(N(C1)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "IC=1C(NC(N(C1)CCCN1C[C@]2(C[C@H]2C1)C1=CC=C(C=C1)C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-Benzoyl-5-iodo-1-{3-[(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hex-3-yl]-propyl}-1H-pyrimidine-2,4-dione (Prep 39, 840 mg, 1.38 mmol) was dissolved in 10% NH3 in MeOH solution (5 mL). The mixture was stirred at room temperature for 1 hour, the solvent was then evaporated under vacuum and the crude puri... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.C1[NH]C[C@H]2C[C@@H]12.c1ccccc1 | HO- | CO.N | null | 1 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)c1=O>CO.N>O=c1[nH]c(=O)n(CCCN2C[C@@H]3C[C@]3(c3ccc(C(F)(F)F)cc3)C2)cc1I |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e06524fe40ad4c5a873fc85d108fc91f | CCC(Cl)Br.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O | O.C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O.C(=O)([O-])[O-].[K+].[K+].BrC(CC)Cl>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCl)=O | Br[CH:18]([CH2:17][CH3:16])[Cl:19].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][nH:15][c:20]1=[O:21]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][n:15]([CH2:16][CH2:17][CH2:18][Cl:19])[c:20]1=[O:21] | CCC(Cl)Br.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 478069da08d3aa5a55e85f606108b025abd756e3819c0b38e0de56530a405f10 | 498fc9fa63817756d78172f2f80442d316dac1e36623b01cda3447ffb87955c4 | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Br-[CH;D3;+0:1](-[Cl;D1;H0:2])-[C:3]-[CH3;D1;+0:4].[O;D1;H0:5]=[C:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[Cl;D1;H0:2]-[CH2;D2;+0:1]-[C:3]-[CH2;D2;+0:4]-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[#7;a:7](-[C:6]=[O;D1;H0:5]):[c:12]:1=[O;D1;H0:13] | 98.1 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep36, 3 g, 8.77 mmol) and K2CO3 (1.2 g, 8.77 mmol) were suspended in dry DMF (45 mL) and stirred at room temperature for 1 h. Then, bromo-chloro-propane (2.7 mL, 17.5 mmol) was added dropwise and the mixture stirred at room temperature overnight. Water was added and the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HBr | CN(C)C=O | null | 1 | CCC(Cl)Br.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>CN(C)C=O>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-be7ca5510b144cf3b4c77a2eaa0cbb21 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O.OB(O)c1cccnc1>>O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCl)=O.N1=CC(=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C=NC=CC1)CCCCl)=O | I[c:12]1[c:10](=[O:11])[n:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[c:25](=[O:26])[n:20]([CH2:21][CH2:22][CH2:23][Cl:24])[cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12](-[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[cH:19... | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O.OB(O)c1cccnc1 | O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccccc1)n1c(=O)[nH]cc(-c2cccnc2)c1=O | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]):[c:5]:[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:9]:1=[O;D1;H0:10].O-B(-O)-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[C:4]-[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:2):[c:9](=[O;D1;H0:10]):[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:5]:1 | 20.3 | [{"value": 20.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C=NC=CC1)CCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.3, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C=NC=CC1)CCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-1-(3-chloro-propyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 41,500 mg, 1.2 mmol) was dissolved in degassed DME-water solution (5-1, 35 mL). Pyridine-3-boronic acid (629 mg, 1.8 mmol), Na2CO3 (380 mg, 3.6 mmol), 2-(dicyclohexylphosphino)biphenyl (84 mg, 0.24 mmol) and Pd(PPh3)4 (250 mg, 0.24 mmol) were added and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.O | null | null | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCl)c1=O.OB(O)c1cccnc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.O>O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aded28fcea1046c9808e7f2383fec13a | O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O>>O=c1[nH]c(=O)n(CCCCl)cc1-c1cccnc1 | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C=NC=CC1)CCCCl)=O>>ClCCCN1C(NC(C(=C1)C=1C=NC=CC1)=O)=O | O=C(c1ccccc1)[n:3]1[c:2](=[O:1])[c:12](-[c:13]2[cH:14][cH:15][cH:16][n:17][cH:18]2)[cH:11][n:6]([CH2:7][CH2:8][CH2:9][Cl:10])[c:4]1=[O:5]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1 | O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O | O=c1[nH]c(=O)n(CCCCl)cc1-c1cccnc1 | null | null | CO.N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:7]-[#7;a:6]1:[c:5]:[c:4]:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:8]:1=[O;D1;H0:9] | 66 | [{"value": 66.0, "product": "ClCCCN1C(NC(C(=C1)C=1C=NC=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "ClCCCN1C(NC(C(=C1)C=1C=NC=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-1-(3-Chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dione (Prep42, 90 mg, 0.24 mmol) was dissolved in a solution of 3% NH3 in MeOH (5 mL). The mixture was stirred at room temperature over night, the solvent was then evaporated under vacuum and the residue was passed over a SCX cartridge to give 42 mg of the ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HO- | CO.N | null | null | O=C(c1ccccc1)n1c(=O)c(-c2cccnc2)cn(CCCCl)c1=O>CO.N>O=c1[nH]c(=O)n(CCCCl)cc1-c1cccnc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4c3f16b0bb0c482b95c193d01b240bd6 | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | O.C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCCl>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O | Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][nH:15][c:21]1=[O:22]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][n:15]([CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])[c:21]1=[O:22] | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1=[O;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6](-[C:5]=[O;D1;H0:4]):[c:11]:1=[O;D1;H0:12] | 98 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep36, 2.5 g, 7.3 mmol), K2CO3 (1 g, 7.3 mmol) and 1-bromo-4-chloro-butane (2.10 mL, 18 mmol) were suspended in dry DMF (10 mL). After stirring the reaction at room temperature overnight, water was added and the mixture was extracted with ethyl acetate. The organic phase was d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HBr | CN(C)C=O | null | null | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>CN(C)C=O>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cc0aaa571d0c426fad3879969ab473b0 | Cc1cc(B(O)O)ccn1.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O>>Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1 | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O.CC1=NC=CC(=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C1=CC(=NC=C1)C)CCCCCl)=O | OB(O)[c:4]1[cH:3][c:2]([CH3:1])[n:28][cH:27][cH:26]1.I[c:5]1[cH:6][n:7]([CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13](=[O:14])[n:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]1=[O:25]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][n:7]([CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13](=[O:14])[n:15]([C:16](=[... | Cc1cc(B(O)O)ccn1.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccccc1)n1c(=O)[nH]cc(-c2ccncc2)c1=O | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]):[c:5]:[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:9]:1=[O;D1;H0:10].O-B(-O)-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15](-[C;D1;H3:16]):[c:17]:1>>[C:4]-[#7;a:3]1:[c:5]:[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:9](=[O;D1;H0:10]):[c;H0;D3;+0:1](-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[#7;a:14]:[c:15](-[C;D1... | 25.1 | [{"value": 25.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C1=CC(=NC=C1)C)CCCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.1, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C1=CC(=NC=C1)C)CCCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 44, 433 mg, 1 mmol) was dissolved in degassed DME-water solution (5-1, 30 mL). 2-methyl-pyridine 4-boronic acid (205 mg, 1.5 mmol), Na2CO3 (212 mg, 2 mmol), 2-(dicyclohexylphosphino)biphenyl (70 mg, 0.2 mmol) and Pd(PPh3)4 (231 mg, 0.2 mmol) were added a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1cncnc1 | c1ccncc1.c1cncnc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.O | null | null | Cc1cc(B(O)O)ccn1.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.O>Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-67e7e7cac166413a9063e2eaf416ec76 | Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1>>Cc1cc(-c2cn(CCCCCl)c(=O)[nH]c2=O)ccn1 | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C1=CC(=NC=C1)C)CCCCCl)=O>>ClCCCCN1C(NC(C(=C1)C1=CC(=NC=C1)C)=O)=O | O=C(c1ccccc1)[n:15]1[c:13](=[O:14])[n:7]([CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[n:20][cH:19][cH:18]2)[c:16]1=[O:17]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][n:7]([CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[cH:18][cH:19][n:20]1 | Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1 | Cc1cc(-c2cn(CCCCCl)c(=O)[nH]c2=O)ccn1 | null | null | CO.N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1[nH]cc(-c2ccncc2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[c:6]:[c:7]:[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:5]-[#7;a:4]1:[c:6]:[c:7]:[c:8](=[O;D1;H0:9]):[nH;D2;+0:1]:[c:2]:1=[O;D1;H0:3] | null | [] | null | null | 3 | HOUR | 3-Benzoyl-1-(4-chloro-butyl)-5-(2-methyl-pyridin-4-yl)-1H-pyrimidine-2,4-dione (Prep 45, 100 mg, 0.25 mmol) was dissolved in a solution of 3% NH3 in MeOH (5 mL). The mixture was stirred at room temperature for 3 hours, the solvent was then evaporated under vacuum to give the title compound that was used in the next ste... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HO- | CO.N | null | 3 | Cc1cc(-c2cn(CCCCCl)c(=O)n(C(=O)c3ccccc3)c2=O)ccn1>CO.N>Cc1cc(-c2cn(CCCCCl)c(=O)[nH]c2=O)ccn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bf93c613eb994ddbbb7ea5a73a4f3a52 | Cc1ncccc1B(O)O.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O>>Cc1ncccc1-c1cn(CCCCCl)c(=O)n(C(=O)c2ccccc2)c1=O | CC1=NC=CC=C1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CC1=NC=CC=C1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C(=NC=CC1)C)CCCCCl)=O | OB(O)[c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1.I[c:8]1[cH:9][n:10]([CH2:11][CH2:12][CH2:13][CH2:14][Cl:15])[c:16](=[O:17])[n:18]([C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]1=[O:28]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10]([CH2:11][CH2:12][CH2:13][CH2:14][Cl:15])[c:16](=[O:... | Cc1ncccc1B(O)O.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | Cc1ncccc1-c1cn(CCCCCl)c(=O)n(C(=O)c2ccccc2)c1=O | null | C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC... | COCCOC.O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccccc1)n1c(=O)[nH]cc(-c2cccnc2)c1=O | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]):[c:5]:[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:9]:1=[O;D1;H0:10].O-B(-O)-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:1-[C;D1;H3:17]>>[C:4]-[#7;a:3]1:[c:5]:[#7;a:6](-[C:7]=[O;D1;H0:8]):[c:9](=[O;D1;H0:10]):[c;H0;D3;+0:1](-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:2... | 66.4 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C(=NC=CC1)C)CCCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C(=NC=CC1)C)CCCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 44, 541 mg, 1.25 mmol) was dissolved in degassed DME-water solution (5-1, 37.5 mL). 2-Methyl-pyridine 3-boronic acid (325 mg, 1.9 mmol), Na2CO3 (265 mg, 2.5 mmol), 2-(dicyclohexylphosphino)biphenyl (52 mg, 0.15 mmol) and Pd(PPh3)4 (288 mg, 0.25 mmol) wer... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1cncnc1 | c1ccncc1.c1cncnc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HI.B | C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC... | null | null | Cc1ncccc1B(O)O.O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O>C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P... |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0f22eac7e945439c9f2dceee9d0e4fd3 | Cc1ncccc1-c1cn(CCCCCl)c(=O)n(C(=O)c2ccccc2)c1=O>>Cc1ncccc1-c1cn(CCCCCl)c(=O)[nH]c1=O | C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)C=1C(=NC=CC1)C)CCCCCl)=O>>ClCCCCN1C(NC(C(=C1)C=1C(=NC=CC1)C)=O)=O | O=C(c1ccccc1)[n:18]1[c:16](=[O:17])[n:10]([CH2:11][CH2:12][CH2:13][CH2:14][Cl:15])[cH:9][c:8](-[c:7]2[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]2)[c:19]1=[O:20]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10]([CH2:11][CH2:12][CH2:13][CH2:14][Cl:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20] | Cc1ncccc1-c1cn(CCCCCl)c(=O)n(C(=O)c2ccccc2)c1=O | Cc1ncccc1-c1cn(CCCCCl)c(=O)[nH]c1=O | null | null | CO.N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[c:6]:[c:7]:[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:5]-[#7;a:4]1:[c:6]:[c:7]:[c:8](=[O;D1;H0:9]):[nH;D2;+0:1]:[c:2]:1=[O;D1;H0:3] | 93.6 | [{"value": 90.0, "product": "ClCCCCN1C(NC(C(=C1)C=1C(=NC=CC1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "ClCCCCN1C(NC(C(=C1)C=1C(=NC=CC1)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3-Benzoyl-1-(4-chloro-butyl)-5-(2-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione (Prep 47, 330 mg, 0.8 mmol) was dissolved in a solution of 3% NH3 in MeOH (15 mL). The mixture was stirred at room temperature for 3 hours, the solvent was then evaporated under vacuum. The residue was redissolved in MeOH and filtered on a S... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HO- | CO.N | null | 3 | Cc1ncccc1-c1cn(CCCCCl)c(=O)n(C(=O)c2ccccc2)c1=O>CO.N>Cc1ncccc1-c1cn(CCCCCl)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aee16765237f4c5d918624d6c4d3c6ad | COc1ncc(B(O)O)c(OC)n1.Cc1cccc(Br)n1>>COc1ncc(-c2cccc(C)n2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.BrC1=NC(=CC=C1)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C1=NC(=CC=C1)C | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].Br[c:7]1[cH:8][cH:9][cH:10][c:11]([CH3:12])[n:13]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH3:12])[n:13]2)[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Cc1cccc(Br)n1 | COc1ncc(-c2cccc(C)n2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[#8:12]>>[#8:12]-[c:11]1:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 47.7 | [{"value": 47.0, "product": "COC1=NC=C(C(=N1)OC)C1=NC(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "COC1=NC=C(C(=N1)OC)C1=NC(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Di-methoxy-pyrimidine-5-boronic acid (500 mg, 2.72 mmol) was dissolved in degassed n-PrOH (40 mL) and then 2-bromo-6-methylpyridine (660 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 0.22 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was ev... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1cccc(Br)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccc(C)n2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-16bfe81ae0474d5ca77c970c1104e47c | CCCC(Cl)Br.Cc1cccc(-c2c[nH]c(=O)[nH]c2=O)n1>>Cc1cccc(-c2cn(CCCCCl)c(=O)[nH]c2=O)n1 | Cl.CC1=CC=CC(=N1)C=1C(NC(NC1)=O)=O.BrC(CCC)Cl.C(=O)([O-])[O-].[K+].[K+].CC1=CC=CC(=N1)C=1C(NC(NC1)=O)=O.BrC(CCC)Cl.C(=O)([O-])[O-].[K+].[K+]>>ClCCCCN1C(NC(C(=C1)C1=NC(=CC=C1)C)=O)=O | Br[CH:10]([CH2:11][CH2:12][CH3:13])[Cl:14].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][nH:9][c:15](=[O:16])[nH:17][c:18]2=[O:19])[n:20]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[c:15](=[O:16])[nH:17][c:18]2=[O:19])[n:20]1 | CCCC(Cl)Br.Cc1cccc(-c2c[nH]c(=O)[nH]c2=O)n1 | Cc1cccc(-c2cn(CCCCCl)c(=O)[nH]c2=O)n1 | null | null | O.CN(C)C=O | Functional Group Interconversion | OtherReaction | 1381f1b46a26fe585ca61b0b67059934aa8a4ee821617b5fee5805936d2a4900 | 6057d7fb75624930c9e41a46967dce14902ce53987bcfcd5587c4c1a79bea4df | O=c1[nH]cc(-c2ccccn2)c(=O)[nH]1 | Br-[CH;D3;+0:1](-[Cl;H0;D1;+0:2])-[C:3]-[C:4]-[CH3;D1;+0:5].[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[Cl;H0;D1;+0:2]-[CH2;D2;+0:5]-[C:4]-[C:3]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[#7;a:8]:[c:7]:1=[O;D1;H0:6] | 157.1 | [{"value": 43.0, "product": "ClCCCCN1C(NC(C(=C1)C1=NC(=CC=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 157.1, "product": "ClCCCCN1C(NC(C(=C1)C1=NC(=CC=C1)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 50, 50 mg, 0.208 mmol) and K2CO3 (43 mg, 0.312 mmol) were suspended in dry DMF (2 mL) and stirred for 1 h at room temperature. Then a solution of bromo-chloro-butane (71.3 mg, 0.416 mmol) in dry DMF (0.5 mL) was added dropwise and the mixture stirred... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HBr | O.CN(C)C=O | null | 1 | CCCC(Cl)Br.Cc1cccc(-c2c[nH]c(=O)[nH]c2=O)n1>O.CN(C)C=O>Cc1cccc(-c2cn(CCCCCl)c(=O)[nH]c2=O)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9a8cf9b2892e4ae19622ca043b60c59e | COc1ncc(I)c(OC)n1.Cc1ccccc1B(O)O>>COc1ncc(-c2ccccc2C)c(OC)n1 | IC=1C(=NC(=NC1)OC)OC.CC1=C(C=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C1=C(C=CC=C1)C | I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH3:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(I)c(OC)n1.Cc1ccccc1B(O)O | COc1ncc(-c2ccccc2C)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;D1;H3:12]):[c:13] | 46.3 | [{"value": 46.0, "product": "COC1=NC=C(C(=N1)OC)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.3, "product": "COC1=NC=C(C(=N1)OC)C1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Iodo-2,4-dimethoxy-pyrimidine (1 g, 3.75 mmol) was dissolved in degassed n-PrOH (25 mL) and then 2-methylphenyl boronic acid (766 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 5.67 mmol) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(I)c(OC)n1.Cc1ccccc1B(O)O>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccccc2C)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-40d5786a29a64265a37526cce3d7fda7 | COc1ncc(-c2ccccc2C)c(OC)n1>>Cc1ccccc1-c1c[nH]c(=O)[nH]c1=O | COC1=NC=C(C(=N1)OC)C1=C(C=CC=C1)C>>C1(=C(C=CC=C1)C=1C(NC(NC1)=O)=O)C | C[O:12][c:11]1[n:10][cH:9][c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)[c:14]([O:15]C)[n:13]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][nH:10][c:11](=[O:12])[nH:13][c:14]1=[O:15] | COc1ncc(-c2ccccc2C)c(OC)n1 | Cc1ccccc1-c1c[nH]c(=O)[nH]c1=O | null | null | CO | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5](-[c:6]):[c;H0;D3;+0:7](-[O;H0;D2;+0:8]-C):[n;H0;D2;+0:9]:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5](-[c:6]):[c;H0;D3;+0:7](=[O;H0;D1;+0:8]):[nH;D2;+0:9]:1 | 90.2 | [{"value": 90.0, "product": "C1(=C(C=CC=C1)C=1C(NC(NC1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "C1(=C(C=CC=C1)C=1C(NC(NC1)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,4-dimethoxy-5-o-tolyl-pyrimidine (Prep52, 400 mg, 1.7 mmol) in MeOH (10 mL) 2N HClaq (3 mL) was added. After refluxing for 48 hours, the solvents were evaporated. The crude was triturated with ethyl acetate to give 310 mg of the desired product (90% yield) that was used in the next step without furth... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | Other | CO | null | null | COc1ncc(-c2ccccc2C)c(OC)n1>CO>Cc1ccccc1-c1c[nH]c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-316478c22577439eb2471c1a36ff2cc8 | CCOC(C)(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC>>CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | C(C)OC(NC(C(=COCC)C#N)=O)=O.C(C)OC(CCN)(C)OCC>>C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)(C)OCC | [CH3:1][CH2:2][O:3][C:4]([CH3:5])([CH2:6][CH2:7][NH2:8])[O:18][CH2:19][CH3:20].CCO[CH:9]=[C:10]([C:11]#[N:12])[C:13](=[O:14])[NH:15][C:16](OCC)=[O:17]>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])([CH2:6][CH2:7][n:8]1[cH:9][c:10]([C:11]#[N:12])[c:13](=[O:14])[nH:15][c:16]1=[O:17])[O:18][CH2:19][CH3:20] | CCOC(C)(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC | CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 294eb494ecaef8e3ca4dca852d6073988c8299ff97a84c68a5ea24695be2d73f | 4a855cedd5facbdcee72b4835f1264911b7b12388e618f5335fca61a604f6099 | O=c1cc[nH]c(=O)[nH]1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3]#[N;D1;H0:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-C-C.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[n;H0;D3;+0:12]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3]#[N;D1;H0:4]):[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c;H0;D3;+0:8]:1=[O;D1;H0:9] | 83 | [{"value": 83.0, "product": "C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)(C)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (2-Cyano-3-ethoxy-acryloyl)-carbamic acid ethyl ester (Prep32, 500 mg, 2.3 mmol) was suspended in water (20 mL) and 3,3-diethoxybutylamine (816 μl, 4.7) was added and the mixture warmed at 80° C. for 10 minutes. The reaction mixture was lyophilized and the residue was purified by flash chromatography with petroleum eth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Unsubstituted dicarboximide.Primary amine | null | null | c1cncnc1 | c1cncnc1 | HO- | O | 80 | null | CCOC(C)(CCN)OCC.CCOC=C(C#N)C(=O)NC(=O)OCC>O>CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aed69bfe41c4432fba303d31b332e3f4 | CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC>>N#Cc1cn(CCCC=O)c(=O)[nH]c1=O | C(C)OC(CCN1C(NC(C(=C1)C#N)=O)=O)(C)OCC.O1CCOCC1>>O=C1N(C=C(C(N1)=O)C#N)CCCC=O | CCO[C:8]([CH2:7][CH2:6][n:5]1[cH:4][c:3]([C:2]#[N:1])[c:14](=[O:15])[nH:13][c:11]1=[O:12])([CH3:9])[O:10]CC>>[N:1]#[C:2][c:3]1[cH:4][n:5]([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[c:11](=[O:12])[nH:13][c:14]1=[O:15] | CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC | N#Cc1cn(CCCC=O)c(=O)[nH]c1=O | null | null | null | Miscellaneous | OtherReaction | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1cc[nH]c(=O)[nH]1 | C-C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[CH2;D2;+0:1]-[CH;D2;+0:2]=[O;H0;D1;+0:5] | null | [] | 60 | CELSIUS | null | null | 1-(3,3-Diethoxy-butyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (Prep 54, 200 mg, 0.71 mmol) was dissolved in dioxane (8 mL) and 1N HClaq (1 mL) was added. The mixture was warmed at 60° C. for 20 minutes. The solvents were evaporated, the residue was submitted to lyophilization, to give 150 mg of the titl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1 | HO- | null | 60 | null | CCOC(C)(CCn1cc(C#N)c(=O)[nH]c1=O)OCC>>N#Cc1cn(CCCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-467f17a6508d4a118f67db9676324ab1 | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(Br)cn1>>COc1ncc(-c2ccc(C)nc2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.BrC=1C=NC(=CC1)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C=1C=NC(=CC1)C | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].Br[c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[n:12][cH:13]2)[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(Br)cn1 | COc1ncc(-c2ccc(C)nc2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 62 | [{"value": 62.0, "product": "COC1=NC=C(C(=N1)OC)C=1C=NC(=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (commercially available from Aldrich, 830 mg, 4.5 mmol) was dissolved in degassed n-PrOH (10 mL) and then 3-bromo-6-methylpyridine (600 mg, 3.5 mmol), Na2CO3 (956 mg, 9 mmol), PPh3 (90 mg, 0.35 mmol) and Pd(OAc)2 (78 mg, 0.35 mmol) were added. The suspension was stirred at reflux... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(Br)cn1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccc(C)nc2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-204e0a98af9b49778d661eaac3535d46 | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)cn1>>COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC | BrCCC(OC)OC.Cl.CC1=CC=C(C=N1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].O.BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1C=NC(=CC1)C)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][cH:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)cn1 | COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 48 | [{"value": 48.0, "product": "COC(CCN1C(NC(C(=C1)C=1C=NC(=CC1)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep57, 385 mg, 1.62 mmol), K2CO3 (224 mg, 1.62 mmol) and 3-bromo-1,1dimethoxy-propane (commercially available from Aldrich, 183 mg, 1.0 mmol) were suspended in dry DMF (8 mL). After stirring the reaction at room temperature for 24 hours, additional 3-bro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)cn1>CN(C)C=O>COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-881ba26e21f346b391e93da23a00a417 | COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC>>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)cn1 | COC(CCN1C(NC(C(=C1)C=1C=NC(=CC1)C)=O)=O)OC>>CC1=CC=C(C=N1)C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:11]([CH2:10][CH2:9][n:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:19][cH:18]2)[c:16](=[O:17])[nH:15][c:13]1=[O:14])[O:12]C>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8]([CH2:9][CH2:10][CH:11]=[O:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[cH:18][n:19]1 | COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC | Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)cn1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 45 | [{"value": 45.0, "product": "CC1=CC=C(C=N1)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "CC1=CC=C(C=N1)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione (Prep 58, 240 mg, 0.78 mmol) was dissolved in THF (4 mL) and 1N solution of HClaq (1.5 mL) was added. The mixture was stirred at room temperature for 2 hours and then warmed at 45° C. and stirred for an additional hour at this temperature. After... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | null | 2 | COC(CCn1cc(-c2ccc(C)nc2)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-49aa7eb002944783b9f978f9c7b080b9 | COc1ncc(B(O)O)c(OC)n1.Cc1nc(C)c(I)o1>>COc1ncc(-c2oc(C)nc2C)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.IC1=C(N=C(O1)C)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>CC=1OC(=C(N1)C)C=1C(=NC(=NC1)OC)OC | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].I[c:7]1[o:8][c:9]([CH3:10])[n:11][c:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[o:8][c:9]([CH3:10])[n:11][c:12]2[CH3:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Cc1nc(C)c(I)o1 | COc1ncc(-c2oc(C)nc2C)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | OtherReaction | 033d31a7834d8aa148444683f73a9958a77716f33ce61555569093ea87a1da73 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ncc(-c2cnco2)cn1 | I-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[#7;a:4]:[c:5]:1-[C;D1;H3:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[#7;a:4]:[c:5]:1-[C;D1;H3:6] | 67.1 | [{"value": 66.0, "product": "CC=1OC(=C(N1)C)C=1C(=NC(=NC1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "CC=1OC(=C(N1)C)C=1C(=NC(=NC1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (840 mg, 4.6 mmol) was dissolved in degassed n-PrOH (40 mL) and then 5-iodo-2,4-dimethyl-oxazole (Prep60, 850 mg, 3.8 mmol), Na2CO3 (848 mg, 8 mmol), PPh3 (332 mg, 1.3 mmol) and Pd(OAc)2 (85 mg, 0.38 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1cocn1 | c1cncnc1.c1cocn1 | c1cncnc1.c1cocn1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1nc(C)c(I)o1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2oc(C)nc2C)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-10572850b6114d11ba0fe37e22948765 | COc1ncc(-c2oc(C)nc2C)c(OC)n1>>Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1 | CC=1OC(=C(N1)C)C=1C(=NC(=NC1)OC)OC>>CC=1OC(=C(N1)C)C=1C(NC(NC1)=O)=O | C[O:11][c:10]1[n:9][cH:8][c:7](-[c:6]2[c:4]([CH3:5])[n:3][c:2]([CH3:1])[o:15]2)[c:13]([O:14]C)[n:12]1>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][nH:9][c:10](=[O:11])[nH:12][c:13]2=[O:14])[o:15]1 | COc1ncc(-c2oc(C)nc2C)c(OC)n1 | Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1 | null | null | CO | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cnco2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[c:6](-[c:7](:[#8;a:8]):[c:9]:[#7;a:10]):[c:11]:[n;H0;D2;+0:12]:1>>[#7;a:10]:[c:9]:[c:7](-[c:6]1:[c:11]:[nH;D2;+0:12]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:3]:[c;H0;D3;+0:4]:1=[O;H0;D1;+0:5]):[#8;a:8] | 92.7 | [{"value": 92.0, "product": "CC=1OC(=C(N1)C)C=1C(NC(NC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "CC=1OC(=C(N1)C)C=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine (Prep61, 600 mg, 2.5 mmol) in MeOH (40 mL) 2N HClaq (10 mL) was added. After refluxing the mixture for 3 hours, the solvents were evaporated. The crude was triturated with acetone and filtered to give 480 mg of 5-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1cocn1.c1cncnc1 | Other | CO | null | null | COc1ncc(-c2oc(C)nc2C)c(OC)n1>CO>Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4f6497a025c44772aa97628a9417757c | COC(CCBr)OC.Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1>>COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC | O.CC=1OC(=C(N1)C)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[o:10][c:11]([CH3:12])[n:13][c:14]2[CH3:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[o:10][c:11]([CH3:12])[n:13][c:14]2[CH3:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1 | COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cnco2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 53 | [{"value": 53.0, "product": "COC(CCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.5, "product": "COC(CCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep62, 480 mg, 2.32 mmol) and K2CO3 (320 mg, 2.32 mmol) were suspended in dry DMF (6 ml) and stirred at room temperature for 1 h. A solution of 3-bromo-1,1dimethoxy-propane (467 mg, 2.55 mmol) in dry DMF (2 mL) was added dropwise and the mixture stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cocn1 | HBr | CN(C)C=O | null | 1 | COC(CCBr)OC.Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1>CN(C)C=O>COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-32bf4fdbe827430eb8603188e5851cc8 | COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC>>Cc1nc(C)c(-c2cn(CCC=O)c(=O)[nH]c2=O)o1 | COC(CCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O)OC>>CC=1OC(=C(N1)C)C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:12]([CH2:11][CH2:10][n:9]1[cH:8][c:7](-[c:6]2[c:4]([CH3:5])[n:3][c:2]([CH3:1])[o:19]2)[c:17](=[O:18])[nH:16][c:14]1=[O:15])[O:13]C>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][n:9]([CH2:10][CH2:11][CH:12]=[O:13])[c:14](=[O:15])[nH:16][c:17]2=[O:18])[o:19]1 | COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC | Cc1nc(C)c(-c2cn(CCC=O)c(=O)[nH]c2=O)o1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cnco2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 58 | [{"value": 58.0, "product": "CC=1OC(=C(N1)C)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "CC=1OC(=C(N1)C)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 1 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep63, 150 mg, 0.49 mmol) was dissolved in THF (10 mL) and 1N HClaq (3 mL) was added. The mixture was stirred at 45° C. for 1 hour. After cooling and neutralization with a saturated solution of NaHCO3 the product was extracted with DCM. The... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cocn1.c1cncnc1 | HO- | C1CCOC1 | 45 | 1 | COC(CCn1cc(-c2oc(C)nc2C)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1nc(C)c(-c2cn(CCC=O)c(=O)[nH]c2=O)o1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d5dea396028e4bdbb87f348e3420a44f | Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1.ClCCCCBr>>Cc1nc(C)c(-c2cn(CCCCCl)c(=O)[nH]c2=O)o1 | O.C(=O)([O-])[O-].[K+].[K+].CC=1OC(=C(N1)C)C=1C(NC(NC1)=O)=O.BrCCCCCl>>ClCCCCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][nH:9][c:15](=[O:16])[nH:17][c:18]2=[O:19])[o:20]1.Br[CH2:10][CH2:11][CH2:12][CH2:13][Cl:14]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[c:15](=[O:16])[nH:17][c:18]2=[O:19])[o:20]1 | Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1.ClCCCCBr | Cc1nc(C)c(-c2cn(CCCCCl)c(=O)[nH]c2=O)o1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cnco2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 47 | [{"value": 47.0, "product": "ClCCCCN1C(NC(C(=C1)C1=C(N=C(O1)C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep61, 300 mg, 1.45 mmol) was dissolved in dry DMF (4 ml) and K2CO3 (300 mg, 2.17 mmol) was added. The mixture was stirred at room temperature for 1 h, then a solution of 1-bromo-4-chloro-butane (commercially available from Aldrich, 496 mg, 2.9 mmol) in dry DMF (1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cocn1.c1cncnc1 | HBr | CN(C)C=O | null | 1 | Cc1nc(C)c(-c2c[nH]c(=O)[nH]c2=O)o1.ClCCCCBr>CN(C)C=O>Cc1nc(C)c(-c2cn(CCCCCl)c(=O)[nH]c2=O)o1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-da7cc571d86c471794517e072fdfd449 | COc1ncc(I)c(OC)n1.OB(O)c1ccncc1F>>COc1ncc(-c2ccncc2F)c(OC)n1 | IC=1C(=NC(=NC1)OC)OC.FC=1C=NC=CC1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>FC=1C=NC=CC1C=1C(=NC(=NC1)OC)OC | I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].OB(O)[c:7]1[cH:8][cH:9][n:10][cH:11][c:12]1[F:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(I)c(OC)n1.OB(O)c1ccncc1F | COc1ncc(-c2ccncc2F)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2cncnc2)ccn1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1-[F;D1;H0:14]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1-[F;D1;H0:14] | 93 | [{"value": 93.0, "product": "FC=1C=NC=CC1C=1C(=NC(=NC1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Iodo-2,4-dimethoxy-pyrimidine (commercially available from Matrix, 905 mg, 3.4 mmol) was dissolved in degassed n-PrOH (24 ml) and then 3-fluoropyridine-4-boronic acid (715 mg, 5.1 mmol), Na2CO3 (721 mg, 6.8 mmol), PPh3 (84 mg, 0.34 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 1.5 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(I)c(OC)n1.OB(O)c1ccncc1F>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccncc2F)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f57bbcdae829410bbe9f1eaea270f0fb | COc1ncc(-c2ccncc2F)c(OC)n1.ClCCl>>Cl.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1 | FC=1C=NC=CC1C=1C(=NC(=NC1)OC)OC.CC(C)O.C(Cl)Cl>>Cl.FC=1C=NC=CC1C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:13])[c:14]([O:15]C)[n:16]1.ClC[Cl:1]>>[ClH:1].[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:13])[c:14](=[O:15])[nH:16]1 | COc1ncc(-c2ccncc2F)c(OC)n1.ClCCl | Cl.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1 | null | null | CO | Acylation | OtherReaction | 97a48b445203d7fd8bb560e8ddac12e30c66a86766c7f06c929109d06bc20864 | e75f678912b9df9180ec22a66343218b5a501566bd1812df18dfd29ba33f3ca6 | O=c1[nH]cc(-c2ccncc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9].Cl-C-[Cl;H0;D1;+0:10]>>[ClH;D0;+0:10].[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:6]:[c:7]:[c:8]:1-[c:9] | 85 | [{"value": 85.0, "product": "Cl.FC=1C=NC=CC1C=1C(NC(NC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-(3-Fluoro-pyridin-4-yl)-2,4-dimethoxy-pyrimidine (Prep 66, 725 mg, 3.1 mmol) in MeOH (50 ml) 2N HClaq (20 ml) was added. After refluxing the mixture for 1 hour, the solvents were evaporated and the crude was tritured with hexane then with iPrOH and finally with DCM to give 550 mg of the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HCl | CO | null | null | COc1ncc(-c2ccncc2F)c(OC)n1.ClCCl>CO>Cl.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-139880581b8140598e60dce3f19e2b8f | COC(CCBr)OC.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1>>COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC | C(C)(=O)OCC.C(=O)([O-])[O-].[K+].[K+].Cl.FC=1C=NC=CC1C=1C(NC(NC1)=O)=O.BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C1=C(C=NC=C1)F)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[F:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[F:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1 | COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2ccncc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 22 | [{"value": 22.0, "product": "COC(CCN1C(NC(C(=C1)C1=C(C=NC=C1)F)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.0, "product": "COC(CCN1C(NC(C(=C1)C1=C(C=NC=C1)F)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 67, 243 mg, 1.1 mmol) was dissolved in DMF (2 ml). K2CO3 (153 mg, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. 3-Bromo-1,1dimethoxy-propane (225 mg, 1.11 mmol) was then added and after stirring the reaction at room ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | COC(CCBr)OC.O=c1[nH]cc(-c2ccncc2F)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2987d728ae054e93acdca24ab116c5a0 | COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2ccncc2F)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C1=C(C=NC=C1)F)=O)=O)OC>>FC=1C=NC=CC1C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[F:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[F:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19] | COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2ccncc2F)c(=O)[nH]c1=O | null | null | CO | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2ccncc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | null | null | 16 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(3-fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione (Prep 68, 75 mg, 0.24 mmol) was dissolved in MeOH (2 ml) and 1N HClaq (500 μl) was added. The mixture was stirred at room temperature for 16 hours. MeOH was evaporated under vacuum and dioxane was added. After heating the mixture at 60° C. for 6... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccncc1 | HO- | CO | null | 16 | COC(CCn1cc(-c2ccncc2F)c(=O)[nH]c1=O)OC>CO>O=CCCn1cc(-c2ccncc2F)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5d2ba8741cdc4601a6f678054ff65ceb | COc1ncc(I)c(OC)n1.OB(O)c1cc(F)cnc1Cl>>COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1 | ClC1=NC=C(C=C1B(O)O)F.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.IC=1C(=NC(=NC1)OC)OC>>ClC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)F | I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17].OB(O)[c:7]1[cH:8][c:9]([F:10])[cH:11][n:12][c:13]1[Cl:14]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][n:12][c:13]2[Cl:14])[c:15]([O:16][CH3:17])[n:18]1 | COc1ncc(I)c(OC)n1.OB(O)c1cc(F)cnc1Cl | COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14] | 27 | [{"value": 27.0, "product": "ClC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.0, "product": "ClC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Iodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(I)c(OC)n1.OB(O)c1cc(F)cnc1Cl>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c791a7054bd249c7b55314689d1cafc9 | COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1>>Cl.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1 | ClC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)F>>Cl.ClC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)F | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][n:12][c:13]2[Cl:1])[c:15]([O:16]C)[n:17]1>>[ClH:1].[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][n:12][c:13]2[Cl:14])[c:15](=[O:16])[nH:17]1 | COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1 | Cl.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1 | null | null | CO | Functional Group Addition | OtherReaction | 117aef8520bc78daea2896b76d3cc4fe4fd7698a6e68a4ef259a631a7d2ad9c7 | 1189afaec490b1f202f085ea4c64ff805f9bea5c52f4a029ba16cc01ecffd9ab | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9](:[c:10]):[c;H0;D3;+0:11](-[Cl;H0;D1;+0:12]):[#7;a:13]:[c:14]>>[Cl;D1;H0:15]-[c;H0;D3;+0:11](:[#7;a:13]:[c:14]):[c:9](-[c:8]1:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D3;+0:2]... | 201.2 | [{"value": 97.0, "product": "Cl.ClC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 201.2, "product": "Cl.ClC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-(2-chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep 70, 240 mg, 0.89 mmol) in MeOH (20 ml) 10% HClaq (15 ml) was added. After refluxing the mixture for 8 hours, the solvents were evaporated and the crude was triturated with ethyl acetate to give 249 mg of the title compound (97% yield)
Co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic halide | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | Other | CO | null | null | COc1ncc(-c2cc(F)cnc2Cl)c(OC)n1>CO>Cl.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-224de5a4eea7482e98c9b75bfc6eabe9 | COC(CCBr)OC.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1>>COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC | O.Cl.ClC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)F.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1C(=NC=C(C1)F)Cl)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([F:12])[cH:13][n:14][c:15]2[Cl:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([F:12])[cH:13][n:14][c:15]2[Cl:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21])[O:22][CH3:2... | COC(CCBr)OC.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1 | COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 48.5 | [{"value": 48.0, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC=C(C1)F)Cl)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC=C(C1)F)Cl)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(2-Chloro-5-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep71, 249 mg, 0.9 mmol), K2CO3 (124 mg, 0.9 mmol) and 3-bromo-1,1dimethoxy-propane (205 mg, 1.1 mmol) were suspended in DMF (3 ml). After stirring the reaction at room temperature for 18 hours, water was added. The aqueous layer washed with die... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(CCBr)OC.O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fd3ed7d83af441a785bb5c389bfe5897 | COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C=1C(=NC=C(C1)F)Cl)=O)=O)OC>>ClC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)F | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([F:11])[cH:12][n:13][c:14]2[Cl:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([F:11])[cH:12][n:13][c:14]2[Cl:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20] | COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 104.3 | [{"value": 93.0, "product": "ClC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "ClC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(2-chloro-5-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione (Prep72, 100 mg, 0.29 mmol) was dissolved in THF (3 ml) and 2N HClaq (0.5 ml) was added. The solution was stirred at room temperature for 1 hour. THF was evaporated under vacuum and the aqueous residue was lyophilized to give 90 mg of a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccncc1 | HO- | C1CCOC1 | null | 1 | COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f8171c7006b0492aa5e0fccdfb9481a4 | COc1ncc(B(O)O)c(OC)n1.Fc1cccc(Br)n1>>COc1ncc(-c2cccc(F)n2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.BrC1=NC(=CC=C1)F.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>FC1=CC=CC(=N1)C=1C(=NC(=NC1)OC)OC | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].Br[c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[n:13]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[n:13]2)[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Fc1cccc(Br)n1 | COc1ncc(-c2cccc(F)n2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[#8:12]>>[#8:12]-[c:11]1:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 57.6 | [{"value": 52.0, "product": "FC1=CC=CC(=N1)C=1C(=NC(=NC1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "FC1=CC=CC(=N1)C=1C(=NC(=NC1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (966 mg, 5.3 mmol) was dissolved in degassed n-PrOH (60 ml) and then 2-bromo-6-fluoropyridine (850 mg, 4.8 mmol), Na2CO3 (1.676 g, 15.8 mmol), PPh3 (400 mg, 1.52 mmol) and Pd(OAc)2 (116 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated u... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Fc1cccc(Br)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccc(F)n2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-52433a06d31e46f9a555363b4c4a650d | COc1ncc(-c2cccc(F)n2)c(OC)n1>>O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1 | FC1=CC=CC(=N1)C=1C(=NC(=NC1)OC)OC.Cl>>Cl.FC1=CC=CC(=N1)C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[n:13]2)[c:14]([O:15]C)[n:16]1>>[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[n:13]2)[c:14](=[O:15])[nH:16]1 | COc1ncc(-c2cccc(F)n2)c(OC)n1 | O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2ccccn2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9]:[#7;a:10]>>[#7;a:10]:[c:9]-[c:8]1:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | 84 | [{"value": 84.0, "product": "Cl.FC1=CC=CC(=N1)C=1C(NC(NC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine (Prep74, 230 mg, 0.98 mmol) was dissolved in a solution of 4N HCl in dioxane (4 ml). After refluxing the reaction mixture for 1 hour, the solvent was removed under vacuum to give 200 mg of the title compound (84% yield)
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | Other | O1CCOCC1 | null | null | COc1ncc(-c2cccc(F)n2)c(OC)n1>O1CCOCC1>O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e9f8b59231f648d7990315cef63ab5fc | COC(CCBr)OC.O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1>>COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC | O.Cl.FC1=CC=CC(=N1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C1=NC(=CC=C1)F)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[n:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[n:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1 | COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2ccccn2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 70.6 | [{"value": 70.0, "product": "COC(CCN1C(NC(C(=C1)C1=NC(=CC=C1)F)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "COC(CCN1C(NC(C(=C1)C1=NC(=CC=C1)F)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5-(6-Fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep75, 200 mg, 0.82 mmol), and K2CO3 (169 mg, 1.23 mmol) in DMF (4 ml) was stirred 1 hour at room temperature. 3-Bromo-1,1dimethoxy-propane (165 mg, 0.90 mmol) was added and stirring was continued for 48 hours. Water (50 ml) was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | COC(CCBr)OC.O=c1[nH]cc(-c2cccc(F)n2)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f282dd20ba1842b0bc285859e2867010 | COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C1=NC(=CC=C1)F)=O)=O)OC>>FC1=CC=CC(=N1)C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19] | COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2ccccn2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 111.4 | [{"value": 111.4, "product": "FC1=CC=CC(=N1)C=1C(NC(N(C1)CCC=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(6-fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione (Prep76, 179 mg, 0.58 mmol) was dissolved in THF (4 ml) and 2N HClaq (0.5 ml) was added. The solution was then stirred at room temperature for 2 hours. THF was evaporated under vacuum and the aqueous residue was lyophilized to give 170 mg of a y... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccncc1 | HO- | C1CCOC1 | null | 2 | COC(CCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2cccc(F)n2)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9c661d50fd2d4b33b0dcf9a476560655 | CC1(C)OB(c2cccc(C#N)n2)OC1(C)C.COc1ncc(I)c(OC)n1>>COc1ncc(-c2cccc(C#N)n2)c(OC)n1 | IC=1C(=NC(=NC1)OC)OC.C(#N)C1=CC=CC(=N1)B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C1=CC=CC(=N1)C#N | CC1(C)OB([c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]#[N:13])[n:14]2)OC1(C)C.I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]#[N:13])[n:14]2)[c:15]([O:16][CH3:17])[n:18]1 | CC1(C)OB(c2cccc(C#N)n2)OC1(C)C.COc1ncc(I)c(OC)n1 | COc1ncc(-c2cccc(C#N)n2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic esters | bf89c9ddce3ab813b2024bc8034bd45b5019f9cfaec1d935d12db39f3580d27f | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cncnc2)nc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[#8:12]>>[#8:12]-[c:11]1:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 44 | [{"value": 44.0, "product": "COC1=NC=C(C(=N1)OC)C1=CC=CC(=N1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "COC1=NC=C(C(=N1)OC)C1=CC=CC(=N1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Iodo-2,4-dimethoxy-pyrimidine (500 mg, 1.88 mmol) was dissolved in degassed n-PrOH (40 ml) and then 6-cyano-pyridine-2-boronic acid pinacol ester (650 mg, 2.82 mmol), Na2CO3 (598 mg, 5.64 mmol), PPh3 (164 mg, 0.62 mmol) and Pd(OAc)2 (42 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 3 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccncc1.c1cncnc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | CC1(C)OB(c2cccc(C#N)n2)OC1(C)C.COc1ncc(I)c(OC)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccc(C#N)n2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-99bac3bd46b747efbe532d4ce15019df | Clc1ccc(C23CNCC2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O | ClC1=CC=C(C=C1)C12CNCC2C1.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].IC=1C(N(C(N(C1)CCC=O)=O)C(=O)C1=CC=CC=C1)=O>>ClC1=CC=C(C=C1)C12CN(CC2C1)CCCN1C(N(C(C(=C1)I)=O)C(=O)C1=CC=CC=C1)=O | [NH:19]1[CH2:20][CH:21]2[CH2:22][C:23]2([c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[CH2:31]1.O=[CH:18][CH2:17][CH2:16][n:15]1[cH:14][c:12]([I:13])[c:10](=[O:11])[n:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[c:32]1=[O:33]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]... | Clc1ccc(C23CNCC2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O | null | null | O.ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | eb674734f1ebadd4d32e44c14db0a0b831b3b3d111dda1e97de1b3b78a8bc6d0 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(c1ccccc1)n1c(=O)ccn(CCCN2CC3CC3(c3ccccc3)C2)c1=O | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | 0 | CELSIUS | 4 | HOUR | 1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexane (racemate, reference procedure for preparation reported in WO2005/080382, 136 mg, 0.703 mmol), acetic acid (0.060 mL, 1.055 mmol), and sodium triacetoxyborohydride (164 mg, 0.774 mmol) were added at 0° C. to a solution of 3-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1NCC2CC12 | C1[NH]CC2CC12 | c1ccccc1.c1cncnc1.C1[NH]CC2CC12.c1ccccc1 | Other | O.ClCCCl | 0 | 4 | Clc1ccc(C23CNCC2C3)cc1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>O.ClCCCl>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-748fbad2856e4ad48b9a9f0a0b0784a7 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O>>O=c1[nH]c(=O)n(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)cc1I | ClC1=CC=C(C=C1)C12CN(CC2C1)CCCN1C(N(C(C(=C1)I)=O)C(=O)C1=CC=CC=C1)=O.CO>>ClC1=CC=C(C=C1)C12CN(CC2C1)CCCN1C(NC(C(=C1)I)=O)=O | O=C(c1ccccc1)[n:3]1[c:2](=[O:1])[c:24]([I:25])[cH:23][n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH2:13][C:14]3([c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[CH2:22]2)[c:4]1=[O:5]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH2:13][C:14]3([c:15]3[cH:16][cH:17][c:18](... | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O | O=c1[nH]c(=O)n(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)cc1I | null | null | N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1ccn(CCCN2CC3CC3(c3ccccc3)C2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:7]-[#7;a:6]1:[c:5]:[c:4]:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:8]:1=[O;D1;H0:9] | 83.6 | [{"value": 4.97, "product": "ClC1=CC=C(C=C1)C12CN(CC2C1)CCCN1C(NC(C(=C1)I)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "ClC1=CC=C(C=C1)C12CN(CC2C1)CCCN1C(NC(C(=C1)I)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | (1R,5S/1S,5R)-(1-{3-[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hex-3-yl]propyl}-5-iodo-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (Prep 80, 190 mg, 0.330 mmol) was dissolved in 3% ammonia in MeOH (4 ml, 5.55 mmol). The mixture was stirred at room temperature for 3 hours the solvent was then evaporated under vacuum and t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.C1[NH]CC2CC12.c1ccccc1 | HO- | N | null | 3 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)c1=O>N>O=c1[nH]c(=O)n(CCCN2CC3CC3(c3ccc(Cl)cc3)C2)cc1I |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3489754114e34fda9f6da7d4c1416108 | FC(F)(F)c1cccc(C23CNCC2C3)c1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O | IC=1C(N(C(N(C1)CCC=O)=O)C(=O)C1=CC=CC=C1)=O.FC(C=1C=C(C=CC1)C12CNCC2C1)(F)F.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>IC=1C(N(C(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)C(=O)C1=CC=CC=C1)=O | [NH:19]1[CH2:20][CH:21]2[CH2:22][C:23]2([c:24]2[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]2)[CH2:34]1.O=[CH:18][CH2:17][CH2:16][n:15]1[cH:14][c:12]([I:13])[c:10](=[O:11])[n:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[c:35]1=[O:36]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1... | FC(F)(F)c1cccc(C23CNCC2C3)c1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O | null | null | C(=O)(O)[O-].[Na+].ClCCCl.CC(=O)O | Heteroatom Alkylation and Arylation | reductive amination | eb674734f1ebadd4d32e44c14db0a0b831b3b3d111dda1e97de1b3b78a8bc6d0 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(c1ccccc1)n1c(=O)ccn(CCCN2CC3CC3(c3ccccc3)C2)c1=O | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | 46.6 | [{"value": 46.6, "product": "IC=1C(N(C(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)C(=O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | HOUR | To a solution of 3-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(2H)-pyrimidinyl]propanal (P38, 350 mg, 0.88 mmol) and (1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (racemate, reference procedure for preparation reported in WO2005/080382, 200 mg, 0.88 mmol) in dry DCE (10 ml), AcOH was added and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1NCC2CC12 | C1[NH]CC2CC12 | c1ccccc1.c1cncnc1.C1[NH]CC2CC12.c1ccccc1 | Other | C(=O)(O)[O-].[Na+].ClCCCl.CC(=O)O | 0 | 4 | FC(F)(F)c1cccc(C23CNCC2C3)c1.O=CCCn1cc(I)c(=O)n(C(=O)c2ccccc2)c1=O>C(=O)(O)[O-].[Na+].ClCCCl.CC(=O)O>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-081bd455c8474bb09558117224f90bfc | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O>>O=c1[nH]c(=O)n(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)cc1I | IC=1C(N(C(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)C(=O)C1=CC=CC=C1)=O.CO>>IC=1C(NC(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)=O | O=C(c1ccccc1)[n:3]1[c:2](=[O:1])[c:27]([I:28])[cH:26][n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH2:13][C:14]3([c:15]3[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]3)[CH2:25]2)[c:4]1=[O:5]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH2:13][C:14]3([c:15]3... | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O | O=c1[nH]c(=O)n(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)cc1I | null | null | N | Reduction | OtherReaction | 7db9ebe59cf5ebb257885bae2e456c67984d8945478a1d67d176274155c8c422 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=c1ccn(CCCN2CC3CC3(c3ccccc3)C2)c(=O)[nH]1 | O=C(-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9])-c1:c:c:c:c:c:1>>[C:7]-[#7;a:6]1:[c:5]:[c:4]:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:8]:1=[O;D1;H0:9] | 81 | [{"value": 81.0, "product": "IC=1C(NC(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "IC=1C(NC(N(C1)CCCN1CC2(CC2C1)C1=CC(=CC=C1)C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | (1R,5S/1S,5R) 5-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione (Prep82, 250 mg, 0.410 mmol) was dissolved in 3% ammonia in MeOH, (4 mL, 5.55 mmol). The mixture was stirred at room temperature for 3 hours, the solvent was then evaporated under v... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.C1[NH]CC2CC12.c1ccccc1 | HO- | N | null | 3 | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)c1=O>N>O=c1[nH]c(=O)n(CCCN2CC3CC3(c3cccc(C(F)(F)F)c3)C2)cc1I |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c4c1cbbe3d4c4342ab9166f0952850e1 | COc1ncc(Br)c(OC)n1.OB(O)c1cccnc1F>>COc1ncc(-c2cccnc2F)c(OC)n1 | BrC=1C(=NC(=NC1)OC)OC.FC1=NC=CC=C1B(O)O.B(O)O.C([O-])([O-])=O.[K+].[K+]>>FC1=NC=CC=C1C=1C(=NC(=NC1)OC)OC | Br[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[F:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(Br)c(OC)n1.OB(O)c1cccnc1F | COc1ncc(-c2cccnc2F)c(OC)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CCOC(=O)C.O.O1CCOCC1 | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[F;D1;H0:14]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[F;D1;H0:14] | 93.1 | [{"value": 93.1, "product": "FC1=NC=CC=C1C=1C(=NC(=NC1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a mixture of 5-bromo-2,4-bis(methyloxy)pyrimidine (Prep86, 3 g, 13.70 mmol), 2-fluoropyridine-3-boronic acid (1.930 g, 13.70 mmol) and Pd(PPh3)4 (0.791 g, 0.685 mmol), dry 1,4-Dioxane (45 ml) was added followed by potassium carbonate 1M solution (27.4 ml, 27.4 mmol). The mixture was degassed with Argon and then heat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.O1CCOCC1 | 90 | null | COc1ncc(Br)c(OC)n1.OB(O)c1cccnc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.O1CCOCC1>COc1ncc(-c2cccnc2F)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7dfa12c1ad044b53834cd890affd01db | COc1ncc(-c2cccnc2F)c(OC)n1>>O=c1[nH]cc(-c2cccnc2F)c(=O)[nH]1 | FC1=NC=CC=C1C=1C(=NC(=NC1)OC)OC.O1CCOCC1.Cl>>Cl.FC1=NC=CC=C1C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[c:14]([O:15]C)[n:16]1>>[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[c:14](=[O:15])[nH:16]1 | COc1ncc(-c2cccnc2F)c(OC)n1 | O=c1[nH]cc(-c2cccnc2F)c(=O)[nH]1 | null | null | null | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9]:[c:10]:[#7;a:11]>>[#7;a:11]:[c:10]:[c:9]-[c:8]1:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | null | [] | null | null | null | null | A solution of 5-(2-fluoro-3-pyridinyl)-2,4-bis(methyloxy)pyrimidine (Prep87, 2.8 g, 11.90 mmol) in HCl 4M in 1,4dioxane (42 mL, 168 mmol) was heated at 90° C. for 1 h. A white precipitate crashed out of the solution. Volatiles were evaporated under reduced pressure to give title compound, pale yellow solid (2.75 g).
Co... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | Other | null | null | null | COc1ncc(-c2cccnc2F)c(OC)n1>>O=c1[nH]cc(-c2cccnc2F)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-83a8359273f84a0e9c3c5ff492ad4420 | COc1ncc(B(O)O)c(OC)n1.Clc1ccc(I)cn1>>COc1ncc(-c2ccc(Cl)nc2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.ClC1=NC=C(C=C1)I.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>ClC1=CC=C(C=N1)C=1C(=NC(=NC1)OC)OC | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].I[c:7]1[cH:8][cH:9][c:10]([Cl:11])[n:12][cH:13]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[n:12][cH:13]2)[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Clc1ccc(I)cn1 | COc1ncc(-c2ccc(Cl)nc2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.14 g, 6.26 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloro-5-iodopyridine (1 g, 4.2 mmol), Na2CO3 (884 mg, 15.8 mmol), PPh3 (109 mg, 0.42 mmol) and Pd(OAc)2 (46 mg) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Clc1ccc(I)cn1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccc(Cl)nc2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cc13df9cfbaf42eb8dc5d482c222a399 | COc1ncc(-c2ccc(Cl)nc2)c(OC)n1>>Cl.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1 | ClC1=CC=C(C=N1)C=1C(=NC(=NC1)OC)OC>>Cl.ClC1=CC=C(C=N1)C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:1])[n:12][cH:13]2)[c:14]([O:15]C)[n:16]1>>[ClH:1].[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[n:12][cH:13]2)[c:14](=[O:15])[nH:16]1 | COc1ncc(-c2ccc(Cl)nc2)c(OC)n1 | Cl.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1 | null | null | CO | Functional Group Addition | OtherReaction | 117aef8520bc78daea2896b76d3cc4fe4fd7698a6e68a4ef259a631a7d2ad9c7 | 1189afaec490b1f202f085ea4c64ff805f9bea5c52f4a029ba16cc01ecffd9ab | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9]1:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[Cl;H0;D1;+0:13]):[c:14]:[c:15]:1>>[Cl;D1;H0:16]-[c;H0;D3;+0:12]1:[#7;a:11]:[c:10]:[c:9](-[c:8]2:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D... | 193.6 | [{"value": 193.6, "product": "Cl.ClC1=CC=C(C=N1)C=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep90, 4.17 mmol) was dissolved in MeOH (30 ml) and then 2N HClaq (10 ml) was added. After refluxing the reaction mixture for 4 hours, the solvent was removed under vacuum to give 1.05 g of the title compound (quantitative yield).
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic halide | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | Other | CO | null | null | COc1ncc(-c2ccc(Cl)nc2)c(OC)n1>CO>Cl.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cbb08e8ad456443e8d4d55ae46eccee5 | COC(CCBr)OC.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1>>COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC | Cl.ClC1=CC=C(C=N1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>ClC1=CC=C(C=N1)C=1C(NC(N(C1)CCC(OC)OC)=O)=O | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[n:14][cH:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[n:14][cH:15]2)[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1 | COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 40 | [{"value": 40.0, "product": "ClC1=CC=C(C=N1)C=1C(NC(N(C1)CCC(OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "ClC1=CC=C(C=N1)C=1C(NC(N(C1)CCC(OC)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A mixture of 5-(6-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep91, 1.05 g, 4.10 mmol), and K2CO3 (565 mg, 4.10 mmol) in DMF (20 ml) was stirred 20 minutes at room temperature. 3-Bromo-1,1dimethoxy-propane (635 μl, 4.65 mmol) was added in three portions over 6 days. Solvent was then removed under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 0.333333 | COC(CCBr)OC.O=c1[nH]cc(-c2ccc(Cl)nc2)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-06092e2182fb448f8c85e017bcd16aec | COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O | ClC1=CC=C(C=N1)C=1C(NC(N(C1)CCC(OC)OC)=O)=O>>ClC1=CC=C(C=N1)C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[n:13][cH:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[n:13][cH:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19] | COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 40 | CELSIUS | 1.5 | HOUR | 5-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep92, 267 mg, 0.82 mmol) was dissolved in THF (10 ml) and then 1N HClaq (0.82 ml) was added. The solution was stirred at 40° C. for 1.5 hours. TEA (116 μl, 0.83 mmol) was added and the solvent was removed in vacuum at room temperature. Residu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccncc1 | HO- | C1CCOC1 | 40 | 1.5 | COC(CCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2ccc(Cl)nc2)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-39e094d93f7f4d7f97b94ae4898ea550 | COc1ncc(I)c(OC)n1.OB(O)c1cccnc1Cl>>COc1ncc(-c2cccnc2Cl)c(OC)n1 | COC1=NC=C(C(=N1)OC)I.ClC1=NC=CC=C1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>ClC1=NC=CC=C1C=1C(=NC(=NC1)OC)OC | I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[Cl:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[Cl:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(I)c(OC)n1.OB(O)c1cccnc1Cl | COc1ncc(-c2cccnc2Cl)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14] | null | [] | null | null | null | null | 2,4-Dimethoxy-5-iodo-pyrimidine (1 g, 3.76 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloropyridine-3-boronic acid (882 mg, 5.61 mmol), Na2CO3 (800 mg, 7.6 mmol), PPh3 (98 mg, 0.37 mmol) and Pd(OAc)2 (40 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(I)c(OC)n1.OB(O)c1cccnc1Cl>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccnc2Cl)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-de6d100f2dce4cfeb045ece508c2b200 | COc1ncc(-c2cccnc2Cl)c(OC)n1>>Cl.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1 | ClC1=NC=CC=C1C=1C(=NC(=NC1)OC)OC>>Cl.ClC1=NC=CC=C1C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[Cl:1])[c:14]([O:15]C)[n:16]1>>[ClH:1].[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[Cl:13])[c:14](=[O:15])[nH:16]1 | COc1ncc(-c2cccnc2Cl)c(OC)n1 | Cl.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1 | null | null | CO | Functional Group Addition | OtherReaction | 117aef8520bc78daea2896b76d3cc4fe4fd7698a6e68a4ef259a631a7d2ad9c7 | 1189afaec490b1f202f085ea4c64ff805f9bea5c52f4a029ba16cc01ecffd9ab | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9](:[c:10]):[c;H0;D3;+0:11](-[Cl;H0;D1;+0:12]):[#7;a:13]:[c:14]>>[Cl;D1;H0:15]-[c;H0;D3;+0:11](:[#7;a:13]:[c:14]):[c:9](-[c:8]1:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D3;+0:2]... | null | [] | null | null | null | null | 5-(2-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep94, 3.76 mmol) was dissolved in MeOH (10 ml), then 2N HClaq (8 ml) was added. After refluxing the reaction mixture for 4 hours, the solvent was removed under vacuum to give the title compound (quantitative yield)
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic halide | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | Other | CO | null | null | COc1ncc(-c2cccnc2Cl)c(OC)n1>CO>Cl.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ddd01cb341e9463f97cacdc3053be46d | COC(CCBr)OC.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1>>COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC | Cl.ClC1=NC=CC=C1C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>ClC1=NC=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[Cl:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[Cl:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1 | COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 40 | [{"value": 40.0, "product": "ClC1=NC=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.6, "product": "ClC1=NC=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 5-(2-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride salt (Prep95, 803 mg, 3.10 mmol) and K2CO3 (428 mg, 3.10 mmol) in DMF (15 ml), 90% 3-bromo-1,1dimethoxy-propane (516 μl, 3.41 mmol) was added in three portions over 5 days. The mixture was contemporarily stirred at room temperature. Solv... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(CCBr)OC.O=c1[nH]cc(-c2cccnc2Cl)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-815b1655803a4afb9cc70222cbb50008 | COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O | ClC1=NC=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O>>ClC1=NC=CC=C1C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[Cl:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[Cl:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19] | COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 40 | CELSIUS | 1.5 | HOUR | 5-(2-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep96, 150 mg, 0.46 mmol) was dissolved in THF (5.6 ml) and 1N HClaq (0.46 ml) was added. The solution was then stirred at 40° C. for 1.5 hours. TEA (0.067 ml, 0.48 mmol) was added and the solvent was carefully removed in vacuum at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccncc1 | HO- | C1CCOC1 | 40 | 1.5 | COC(CCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2cccnc2Cl)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-12f4a5822159455fbcc84489de49ee47 | COc1ncc(B(O)O)c(OC)n1.Cc1cnc(F)c(Br)c1>>COc1ncc(-c2cc(C)cnc2F)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.FC1=NC=C(C=C1Br)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>FC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)C | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17].Br[c:7]1[cH:8][c:9]([CH3:10])[cH:11][n:12][c:13]1[F:14]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[cH:11][n:12][c:13]2[F:14])[c:15]([O:16][CH3:17])[n:18]1 | COc1ncc(B(O)O)c(OC)n1.Cc1cnc(F)c(Br)c1 | COc1ncc(-c2cc(C)cnc2F)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[F;D1;H0:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[#8:14]>>[#8:14]-[c:13]1:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[F;D1;H0:7] | 33.4 | [{"value": 31.0, "product": "FC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.4, "product": "FC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (842 mg, 4.60 mmol) was dissolved in degassed n-PrOH (55 ml) and then 2-fluoro-3-bromo-5-methylpyridine (800 mg, 4.21 mmol), Na2CO3 (1.46 g, 13.77 mmol), PPh3 (348 mg, 1.33 mmol) and Pd(OAc)2 (101 mg, 0.45 mmol) were added. The suspension was stirred at reflux for 2 hours. After ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1cnc(F)c(Br)c1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cc(C)cnc2F)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d3ebb2c1593c4fd898af205b82c80f21 | COc1ncc(-c2cc(C)cnc2F)c(OC)n1>>Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1 | FC1=NC=C(C=C1C=1C(=NC(=NC1)OC)OC)C.Cl>>Cl.FC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)C | C[O:12][c:11]1[n:10][cH:9][c:8](-[c:7]2[c:5]([F:6])[n:4][cH:3][c:2]([CH3:1])[cH:16]2)[c:14]([O:15]C)[n:13]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([F:6])[c:7](-[c:8]2[cH:9][nH:10][c:11](=[O:12])[nH:13][c:14]2=[O:15])[cH:16]1 | COc1ncc(-c2cc(C)cnc2F)c(OC)n1 | Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5](-[c:6]:[c:7]:[#7;a:8]):[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-C):[n;H0;D2;+0:11]:1>>[#7;a:8]:[c:7]:[c:6]-[c:5]1:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:11]:[c;H0;D3;+0:9]:1=[O;H0;D1;+0:10] | 83 | [{"value": 83.0, "product": "Cl.FC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(2-Fluoro-5-methylpyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep98, 350 mg, 1.4 mmol) was dissolved in a solution of 4N HCl in dioxane solution (5 ml). After refluxing the solution for 30 minutes, the solvent was removed under vacuum to give 300 mg of the title compound as a white powder (83% yield).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | Other | O1CCOCC1 | null | null | COc1ncc(-c2cc(C)cnc2F)c(OC)n1>O1CCOCC1>Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-393ef3ff47e94b2ea6bc61546aef45a0 | COC(CCBr)OC.Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1>>COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC | O.Cl.FC1=NC=C(C=C1C=1C(NC(NC1)=O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>FC1=NC=C(C=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[cH:13][n:14][c:15]2[F:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[cH:13][n:14][c:15]2[F:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21])[O:22][CH3... | COC(CCBr)OC.Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1 | COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 53.3 | [{"value": 53.0, "product": "FC1=NC=C(C=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "FC1=NC=C(C=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5-(2-fluoro-5-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep99, 300 mg, 1.16 mmol), and K2CO3 (241 mg, 1.7 mmol) in DMF (5 ml) was stirred for one hour at room temperature. 3-Bromo-1,1dimethoxy-propane (234 mg, 1.3 mmol) was added and stirring was continued for three days. Water was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | COC(CCBr)OC.Cc1cnc(F)c(-c2c[nH]c(=O)[nH]c2=O)c1>CN(C)C=O>COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c41b290591b04c7c85d7d9b874803ac9 | COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC>>Cc1cnc(F)c(-c2cn(CCC=O)c(=O)[nH]c2=O)c1 | FC1=NC=C(C=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C.O>>FC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)C | CO[CH:13]([CH2:12][CH2:11][n:10]1[cH:9][c:8](-[c:7]2[c:5]([F:6])[n:4][cH:3][c:2]([CH3:1])[cH:20]2)[c:18](=[O:19])[nH:17][c:15]1=[O:16])[O:14]C>>[CH3:1][c:2]1[cH:3][n:4][c:5]([F:6])[c:7](-[c:8]2[cH:9][n:10]([CH2:11][CH2:12][CH:13]=[O:14])[c:15](=[O:16])[nH:17][c:18]2=[O:19])[cH:20]1 | COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC | Cc1cnc(F)c(-c2cn(CCC=O)c(=O)[nH]c2=O)c1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 88 | [{"value": 88.0, "product": "FC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "FC1=NC=C(C=C1C=1C(NC(N(C1)CCC=O)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-(2-Fluoro-5-methyl-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep100, 200 mg, 0.62 mmol) was dissolved in THF (5 ml) and 2N HClaq (1 ml) was added. The solution was stirred at room temperature for 3 hours. The reaction mixture was neutralized with TEA (278 μl, 2 mmol). Water was added and the pr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | null | 3 | COC(CCn1cc(-c2cc(C)cnc2F)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1cnc(F)c(-c2cn(CCC=O)c(=O)[nH]c2=O)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-479b3529179947c7ae9108e5afb47566 | COc1ncc(B(O)O)c(OC)n1.N#Cc1ncccc1Br>>COc1ncc(-c2cccnc2C#N)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.C(#N)C1=NC=CC=C1Br.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C=1C(=NC=CC1)C#N | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17].Br[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[C:13]#[N:14]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[C:13]#[N:14])[c:15]([O:16][CH3:17])[n:18]1 | COc1ncc(B(O)O)c(OC)n1.N#Cc1ncccc1Br | COc1ncc(-c2cccnc2C#N)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7]#[N;D1;H0:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1-[#8:15]>>[#8:15]-[c:14]1:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7]#[N;D1;H0:8] | 79.5 | [{"value": 76.0, "product": "COC1=NC=C(C(=N1)OC)C=1C(=NC=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "COC1=NC=C(C(=N1)OC)C=1C(=NC=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (1 g, 5.46 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-cyano-3-bromopyridine (950 mg, 5.19 mmol), Na2CO3 (1.65 g, 15.56 mmol), PPh3 (393 mg, 1.5 mmol) and Pd(OAc)2 (114 mg, 0.51 mmol) were added. The suspension was stirred at reflux for 3 hours. After cooling, the s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.N#Cc1ncccc1Br>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccnc2C#N)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-60811416b8df4b4dbe46a3d4a9ede2b1 | COc1ncc(-c2cccnc2C#N)c(OC)n1>>N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O | COC1=NC=C(C(=N1)OC)C=1C(=NC=CC1)C#N.Cl>>Cl.O=C1NC=C(C(N1)=O)C=1C(=NC=CC1)C#N | C[O:14][c:13]1[n:12][cH:11][c:10](-[c:9]2[c:4]([C:3]#[N:2])[n:5][cH:6][cH:7][cH:8]2)[c:16]([O:17]C)[n:15]1>>[N:2]#[C:3][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][nH:12][c:13](=[O:14])[nH:15][c:16]1=[O:17] | COc1ncc(-c2cccnc2C#N)c(OC)n1 | N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5](-[c:6]:[c:7]:[#7;a:8]):[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-C):[n;H0;D2;+0:11]:1>>[#7;a:8]:[c:7]:[c:6]-[c:5]1:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:11]:[c;H0;D3;+0:9]:1=[O;H0;D1;+0:10] | 97 | [{"value": 97.0, "product": "Cl.O=C1NC=C(C(N1)=O)C=1C(=NC=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile (Prep102, 1 g, 4.13 mmol) was dissolved in a solution of 4N HCl in dioxane (20 ml). The mixture was refluxed for 45 minutes. The solvent was removed under vacuum to give 1 g of the title compound (97% yield).
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | Other | O1CCOCC1 | null | null | COc1ncc(-c2cccnc2C#N)c(OC)n1>O1CCOCC1>N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f4e4c63036ca423886f85ed817f3c080 | COC(CCBr)OC.N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O>>COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC | O.Cl.O=C1NC=C(C(N1)=O)C=1C(=NC=CC1)C#N.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1C(=NC=CC1)C#N)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[C:15]#[N:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[C:15]#[N:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21])[O:22][CH3:23] | COC(CCBr)OC.N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O | COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 33.2 | [{"value": 33.0, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC=CC1)C#N)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.2, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC=CC1)C#N)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyridine-2-carbonitrile hydrochloride (Prep103, 500 mg, 2 mmol), and K2CO3 (413 mg, 3 mmol) in DMF (7 ml) was stirred for one hour at room temperature. 3-Bromo-1,1dimethoxy-propane (402 mg, 2.2 mmol) was added and stirring continued for 48 hours. Water was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | COC(CCBr)OC.N#Cc1ncccc1-c1c[nH]c(=O)[nH]c1=O>CN(C)C=O>COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9ad38bc707b046e69c350290cb8d3501 | COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC>>N#Cc1ncccc1-c1cn(CCC=O)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C=1C(=NC=CC1)C#N)=O)=O)OC.O>>O=C1N(C=C(C(N1)=O)C=1C(=NC=CC1)C#N)CCC=O | CO[CH:14]([CH2:13][CH2:12][n:11]1[cH:10][c:9](-[c:8]2[c:3]([C:2]#[N:1])[n:4][cH:5][cH:6][cH:7]2)[c:19](=[O:20])[nH:18][c:16]1=[O:17])[O:15]C>>[N:1]#[C:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][n:11]([CH2:12][CH2:13][CH:14]=[O:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20] | COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC | N#Cc1ncccc1-c1cn(CCC=O)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 73 | [{"value": 73.0, "product": "O=C1N(C=C(C(N1)=O)C=1C(=NC=CC1)C#N)CCC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "O=C1N(C=C(C(N1)=O)C=1C(=NC=CC1)C#N)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-[1-(3,3-Dimethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-pyridine-2-carbonitrile (Prep104, 210 mg, 0.66 mmol) was dissolved in THF (5 ml) and 2N HClaq (1 ml) was added. The solution was stirred at room temperature for 2 hours. The reaction mixture was neutralized with TEA. Water was added (1 ml) and the... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | null | 2 | COC(CCn1cc(-c2cccnc2C#N)c(=O)[nH]c1=O)OC>C1CCOC1>N#Cc1ncccc1-c1cn(CCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a4c85c3e9498464ba3062577b6f704f4 | COc1ncc(I)c(OC)n1.Cc1ccc(B(O)O)c(Cl)n1>>COc1ncc(-c2ccc(C)nc2Cl)c(OC)n1 | COC1=NC=C(C(=N1)OC)I.ClC1=NC(=CC=C1B(O)O)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>ClC1=NC(=CC=C1C=1C(=NC(=NC1)OC)OC)C | I[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17].OB(O)[c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[n:12][c:13]2[Cl:14])[c:15]([O:16][CH3:17])[n:18]1 | COc1ncc(I)c(OC)n1.Cc1ccc(B(O)O)c(Cl)n1 | COc1ncc(-c2ccc(C)nc2Cl)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14]>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[Cl;D1;H0:14] | null | [] | null | null | null | null | 2,4-Dimethoxy-5-iodopyrimidine (957 mg, 3.59 mmol) was dissolved in degassed n-PrOH (18 ml) and then 2-chloro-6-methylpyridine-3-boronic acid (923 mg, 5.39 mmol), Na2CO3 (761 mg, 7.2 mmol), PPh3 (94 mg, 0.35 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(I)c(OC)n1.Cc1ccc(B(O)O)c(Cl)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccc(C)nc2Cl)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e1e7da8459184b1886638614ae54b699 | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(Cl)n1>>COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC | BrCCC(OC)OC.Cl.ClC1=NC(=CC=C1C=1C(NC(NC1)=O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC.O>>ClC1=NC(=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][c:15]2[Cl:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][c:15]2[Cl:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21])[O:22][C... | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(Cl)n1 | COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 42 | [{"value": 21.0, "product": "ClC1=NC(=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "ClC1=NC(=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 5-(2-Chloro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep107, 345 mg, 1.27 mmol), K2CO3 (174 mg, 1.27 mmol) and 3-bromo-1,1dimethoxy-propane (86 μl, 0.63 mmol) in DMF (3 ml) was stirred at room temperature overnight. 3-Bromo-1,1dimethoxy-propane (86 μl, 0.63 mmol) was then added and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 8 | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(Cl)n1>CN(C)C=O>COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a71832c0ceba4f5ca3e69a526304511b | COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC>>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(Cl)n1 | ClC1=NC(=CC=C1C=1C(NC(N(C1)CCC(OC)OC)=O)=O)C>>ClC1=NC(=CC=C1C=1C(NC(N(C1)CCC=O)=O)=O)C | CO[CH:11]([CH2:10][CH2:9][n:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:20][c:18]2[Cl:19])[c:16](=[O:17])[nH:15][c:13]1=[O:14])[O:12]C>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8]([CH2:9][CH2:10][CH:11]=[O:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[c:18]([Cl:19])[n:20]1 | COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC | Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(Cl)n1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | null | null | 1 | HOUR | 5-(2-Chloro-6-methyl-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep108, 90 mg, 0.26 mmol) was dissolved in THF (4 ml) and 1N HClaq (265 μl) was added. The solution was then stirred at room temperature for one hour and then warmed at 40° C. for 2.5 hours. TEA (45 μl) was added and the solvent was c... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | null | 1 | COC(CCn1cc(-c2ccc(C)nc2Cl)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(Cl)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a66b7a3b045043e6b8987f76f458da43 | COc1ncc(B(O)O)c(OC)n1.Cc1ccncc1Br>>COc1ncc(-c2cnccc2C)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.CC1=C(C=NC=C1)Br.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>CC1=C(C=NC=C1)C=1C(=NC(=NC1)OC)OC | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:17][c:14]1[O:15][CH3:16].Br[c:7]1[cH:8][n:9][cH:10][cH:11][c:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][c:12]2[CH3:13])[c:14]([O:15][CH3:16])[n:17]1 | COc1ncc(B(O)O)c(OC)n1.Cc1ccncc1Br | COc1ncc(-c2cnccc2C)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[#8:14]>>[#8:14]-[c:13]1:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7] | null | [] | null | null | null | null | 2,4-Dimethoxypyrimidine-5-boronic acid (1.3 g, 7.23 mmol) was dissolved in degassed n-PrOH (20 ml) and then 4-methyl-3-bromo-pyridine (830 g, 4.82 mmol), Na2CO3 (1.02 g, 9.64 mmol), PPh3 (126 mg, 0.48 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated und... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HBr.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1ccncc1Br>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cnccc2C)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-043bcf02c51242e2bb6799e4f06c9ef6 | COC(CCBr)OC.Cc1ccncc1-c1c[nH]c(=O)[nH]c1=O>>COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC | O.Cl.CC1=C(C=NC=C1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1C=NC=CC1C)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:21][CH3:22].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[c:16](=[O:17])[nH:18][c:19]1=[O:20])[O:21][CH3:22] | COC(CCBr)OC.Cc1ccncc1-c1c[nH]c(=O)[nH]c1=O | COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 27 | [{"value": 27.0, "product": "COC(CCN1C(NC(C(=C1)C=1C=NC=CC1C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.9, "product": "COC(CCN1C(NC(C(=C1)C=1C=NC=CC1C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5-(4-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 11, 605 mg, 2.53 mmol) and K2CO3 (349 mg, 2.53 mmol) in DMF (10 ml), 3-bromo-1,1dimethoxy-propane (399 μl, 2.78 mmol) was added in two portions over 2 days and the mixture was contemporarily stirred at room temperature. Water was then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(CCBr)OC.Cc1ccncc1-c1c[nH]c(=O)[nH]c1=O>CN(C)C=O>COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ec7bd10461df43f8b74b205be880fb9b | COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC>>Cc1ccncc1-c1cn(CCC=O)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C=1C=NC=CC1C)=O)=O)OC>>CC1=C(C=NC=C1)C=1C(NC(N(C1)CCC=O)=O)=O | CO[CH:13]([CH2:12][CH2:11][n:10]1[cH:9][c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]2)[c:18](=[O:19])[nH:17][c:15]1=[O:16])[O:14]C>>[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][n:10]([CH2:11][CH2:12][CH:13]=[O:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19] | COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC | Cc1ccncc1-c1cn(CCC=O)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 40 | CELSIUS | 1.5 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(4-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione (Pre112, 100 mg, 0.32 mmol) was dissolved in THF (5 ml) and 1N HClaq (327 μl) was added. The solution was then stirred at 40° C. for 1.5 hours. TEA (45 μl) was added and the solvent was carefully removed in vacuum at room temperature. Residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | 40 | 1.5 | COC(CCn1cc(-c2cnccc2C)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1ccncc1-c1cn(CCC=O)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-77619ad5c1b3442e89739e7524874589 | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(I)c(F)n1>>COc1ncc(-c2ccc(C)nc2F)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.FC1=NC(=CC=C1I)C.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>FC1=NC(=CC=C1C=1C(=NC(=NC1)OC)OC)C | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:18][c:15]1[O:16][CH3:17].I[c:7]1[cH:8][cH:9][c:10]([CH3:11])[n:12][c:13]1[F:14]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[n:12][c:13]2[F:14])[c:15]([O:16][CH3:17])[n:18]1 | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(I)c(F)n1 | COc1ncc(-c2ccc(C)nc2F)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[F;D1;H0:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[#8:14]>>[#8:14]-[c:13]1:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[F;D1;H0:7] | 75.5 | [{"value": 75.0, "product": "FC1=NC(=CC=C1C=1C(=NC(=NC1)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "FC1=NC(=CC=C1C=1C(=NC(=NC1)OC)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.16 g, 6.32 mmol) was dissolved in degassed n-PrOH (22 ml) and then 2-fluoro-6-methyl-3-iodopyridine (870 mg, 3.67 mmol), Na2CO3 (778 mg, 7.34 mmol), PPh3 (96 mg, 0.37 mmol) and Pd(OAc)2 (41 mg added in three portions) were added. The suspension was stirred at reflux for 2.5 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Cc1ccc(I)c(F)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2ccc(C)nc2F)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3fb63e5718eb421b975c24ab94c9dd0a | COc1ncc(-c2ccc(C)nc2F)c(OC)n1>>Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1 | FC1=NC(=CC=C1C=1C(=NC(=NC1)OC)OC)C.Cl>>Cl.FC1=NC(=CC=C1C=1C(NC(NC1)=O)=O)C | C[O:10][c:9]1[n:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:16][c:14]2[F:15])[c:12]([O:13]C)[n:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][nH:8][c:9](=[O:10])[nH:11][c:12]2=[O:13])[c:14]([F:15])[n:16]1 | COc1ncc(-c2ccc(C)nc2F)c(OC)n1 | Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[c:6](-[c:7]:[c:8]:[#7;a:9]):[c:10]:[n;H0;D2;+0:11]:1>>[#7;a:9]:[c:8]:[c:7]-[c:6]1:[c:10]:[nH;D2;+0:11]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[nH;D2;+0:3]:[c;H0;D3;+0:4]:1=[O;H0;D1;+0:5] | 93 | [{"value": 93.0, "product": "Cl.FC1=NC(=CC=C1C=1C(NC(NC1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(2-Fluoro-6-methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep114, 691 mg, 2.76 mmol) was dissolved in 4M HCl in dioxane solution (7 ml). After refluxing the reaction mixture for 45 minutes, the solvent was removed under vacuum to give 667 mg of the title compound (93% yield)
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | Other | O1CCOCC1 | null | null | COc1ncc(-c2ccc(C)nc2F)c(OC)n1>O1CCOCC1>Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d458da18ea134918a5043b29ba1bb36d | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1>>COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC | Cl.FC1=NC(=CC=C1C=1C(NC(NC1)=O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1C(=NC(=CC1)C)F)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:22][CH3:23].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][c:15]2[F:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[n:14][c:15]2[F:16])[c:17](=[O:18])[nH:19][c:20]1=[O:21])[O:22][CH3... | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1 | COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 35 | [{"value": 35.0, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC(=CC1)C)F)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.8, "product": "COC(CCN1C(NC(C(=C1)C=1C(=NC(=CC1)C)F)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 5-(2-fluoro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 15, 667 mg, 2.59 mmol), and K2CO3 (358 mg, 2.59 mmol) in DMF (25 ml) was stirred 30 minutes at room temperature. Then 90% 3-Bromo-1,1dimethoxy-propane (432 μl, 2.85 mmol) was added in three portions during 3 days. Solvent was th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HBr | CN(C)C=O | null | 0.5 | COC(CCBr)OC.Cc1ccc(-c2c[nH]c(=O)[nH]c2=O)c(F)n1>CN(C)C=O>COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fdea2c59003d4981bf3870fcffd1e38d | COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC>>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(F)n1 | COC(CCN1C(NC(C(=C1)C=1C(=NC(=CC1)C)F)=O)=O)OC>>FC1=NC(=CC=C1C=1C(NC(N(C1)CCC=O)=O)=O)C | CO[CH:11]([CH2:10][CH2:9][n:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:20][c:18]2[F:19])[c:16](=[O:17])[nH:15][c:13]1=[O:14])[O:12]C>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8]([CH2:9][CH2:10][CH:11]=[O:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[c:18]([F:19])[n:20]1 | COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC | Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(F)n1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnc2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 40 | CELSIUS | 1 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-(2-fluoro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione (Prep16, 150 mg, 0.46 mmol) was dissolved in THF (4 ml) and then 1N HClaq (0.46 ml) was added. The solution was stirred at 40° C. for 1 hour. TEA (65 μl, 0.47 mmol) was added and the solvent was removed in vacuum at room temperature. Re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1.c1cncnc1 | HO- | C1CCOC1 | 40 | 1 | COC(CCn1cc(-c2ccc(C)nc2F)c(=O)[nH]c1=O)OC>C1CCOC1>Cc1ccc(-c2cn(CCC=O)c(=O)[nH]c2=O)c(F)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-61ffd24111f1436bb4e1532169ca5db5 | COc1ncc(B(O)O)c(OC)n1.Ic1cccnn1>>COc1ncc(-c2cccnn2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.IC=1N=NC=CC1.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C=1N=NC=CC1 | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:16][c:13]1[O:14][CH3:15].I[c:7]1[cH:8][cH:9][cH:10][n:11][n:12]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][n:12]2)[c:13]([O:14][CH3:15])[n:16]1 | COc1ncc(B(O)O)c(OC)n1.Ic1cccnn1 | COc1ncc(-c2cccnn2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | f8f5c061fa0766cf8bf2b56a909373cb6775dd68fbe7d26541aa38df8e9d5b4c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cnnc(-c2cncnc2)c1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 34 | [{"value": 34.0, "product": "COC1=NC=C(C(=N1)OC)C=1N=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.7, "product": "COC1=NC=C(C(=N1)OC)C=1N=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (2.05 g, 11.21 mmol) was dissolved in degassed n-PrOH (80 ml) and then 3-iodo-pyridazine (Prep 119, 2.1 g, 10.19 mmol), Na2CO3 (3.24 g, 30.57 mmol), PPh3 (890 mg, 3.40 mmol) and Pd(OAc)2 (180 mg, 0.8 mmol) were added. The suspension was stirred at reflux for 5 hours. The solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccnnc1 | c1cncnc1.c1ccnnc1 | c1cncnc1.c1ccnnc1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Ic1cccnn1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cccnn2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-71c0abedd2864bd4bb2cd0656b11195b | COC(CCBr)OC.O=c1[nH]cc(-c2cccnn2)c(=O)[nH]1>>COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC | BrCCC(OC)OC.Cl.N1=NC(=CC=C1)C=1C(NC(NC1)=O)=O.BrCCC(OC)OC.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C=1N=NC=CC1)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:20][CH3:21].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19])[O:20][CH3:21] | COC(CCBr)OC.O=c1[nH]cc(-c2cccnn2)c(=O)[nH]1 | COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cccnn2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 24 | [{"value": 24.0, "product": "COC(CCN1C(NC(C(=C1)C=1N=NC=CC1)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "COC(CCN1C(NC(C(=C1)C=1N=NC=CC1)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 5-pyridazin-3-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep121, 656 mg, 2.89 mmol), 3-bromo-1,1dimethoxy-propane (609 mg, 3.33 mmol) and K2CO3 (400 mg, 2.89 mmol) in DMSO (10 ml) was stirred for 24 hours at room temperature. 3-Bromo-1, 1dimethoxy-propane (100 mg, 0.55 mmol) was then added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccnnc1 | HBr | CS(=O)C | null | 24 | COC(CCBr)OC.O=c1[nH]cc(-c2cccnn2)c(=O)[nH]1>CS(=O)C>COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f76a2bda0a47446a84dc131be67e5ed1 | COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2cccnn2)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C=1N=NC=CC1)=O)=O)OC>>O=C1N(C=C(C(N1)=O)C=1N=NC=CC1)CCC=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][n:13]2)[c:14](=[O:15])[nH:16][c:17]1=[O:18]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][n:13]2)[c:14](=[O:15])[nH:16][c:17]1=[O:18] | COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2cccnn2)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cccnn2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | 110.5 | [{"value": 110.5, "product": "O=C1N(C=C(C(N1)=O)C=1N=NC=CC1)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-pyridazin-3-yl-1H-pyrimidine-2,4-dione (Prep122, 200 mg, 0.68 mmol) was dissolved in THF (5 ml) and then 2N HClaq (1 ml) was added. The solution was stirred at room temperature for 1 hour. The solvent was removed under vacuum at room temperature and the residue was lyophilized to give 185 mg ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1ccnnc1 | HO- | C1CCOC1 | null | 1 | COC(CCn1cc(-c2cccnn2)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2cccnn2)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d9b136ad99c54c0f9e509de38773057c | COc1ncc(B(O)O)c(OC)n1.Ic1cnccn1>>COc1ncc(-c2cnccn2)c(OC)n1 | COC1=NC=C(C(=N1)OC)B(O)O.IC1=NC=CN=C1.C(=O)([O-])[O-].[Na+].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>COC1=NC=C(C(=N1)OC)C1=NC=CN=C1 | OB(O)[c:6]1[cH:5][n:4][c:3]([O:2][CH3:1])[n:16][c:13]1[O:14][CH3:15].I[c:7]1[cH:8][n:9][cH:10][cH:11][n:12]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[c:13]([O:14][CH3:15])[n:16]1 | COc1ncc(B(O)O)c(OC)n1.Ic1cnccn1 | COc1ncc(-c2cnccn2)c(OC)n1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)O | C-C Coupling | Suzuki coupling with boronic acids | 22847ae79d33b54b7d7848e0cb904516c91b1fdcfccc8b70670e168d23c93834 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cnc(-c2cncnc2)cn1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 45.4 | [{"value": 45.0, "product": "COC1=NC=C(C(=N1)OC)C1=NC=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.4, "product": "COC1=NC=C(C(=N1)OC)C1=NC=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.33 g, 7.27 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-iodo-pyrazine (1.0 g, 4.85 mmol), Na2CO3 (1.02 g, 9.70 mmol), PPh3 (127 mg, 0.48 mmol) and Pd(OAc)2 (54 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1cnccn1 | c1cncnc1.c1cnccn1 | c1cncnc1.c1cnccn1 | HI.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O | null | null | COc1ncc(B(O)O)c(OC)n1.Ic1cnccn1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)O>COc1ncc(-c2cnccn2)c(OC)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-acd790e96df7459bb8e6de5a9519bbe7 | COc1ncc(-c2cnccn2)c(OC)n1>>O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | COC1=NC=C(C(=N1)OC)C1=NC=CN=C1.Cl>>Cl.N1=C(C=NC=C1)C=1C(NC(NC1)=O)=O | C[O:2][c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[c:13]([O:14]C)[n:15]1>>[O:2]=[c:3]1[nH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[c:13](=[O:14])[nH:15]1 | COc1ncc(-c2cnccn2)c(OC)n1 | O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 18238eb1b1e19f5ed224023cf942e34cf448145e41ccf8dc9c302e39a2bc02d3 | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C):[n;H0;D2;+0:6]:[c:7]:[c:8]:1-[c:9](:[#7;a:10]):[c:11]:[#7;a:12]>>[#7;a:10]:[c:9](-[c:8]1:[c:7]:[nH;D2;+0:6]:[c;H0;D3;+0:4](=[O;H0;D1;+0:5]):[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1]):[c:11]:[#7;a:12] | null | [] | null | null | null | null | 2,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine (Prep124, 481 mg, 2.19 mmol) was dissolved in 4M HCl in dioxane solution (7 ml). After refluxing the reaction mixture for 1 hour, the solvent was removed under vacuum to give the title compound (quantitative yield)
Conditions: See reaction.notes.procedure_details.
Workup: After r... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cnccn1 | Other | O1CCOCC1 | null | null | COc1ncc(-c2cnccn2)c(OC)n1>O1CCOCC1>O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8a7008fcf016486bb7b985cf8340c0ce | COC(CCBr)OC.O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1>>COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC | O.Cl.N1=C(C=NC=C1)C=1C(NC(NC1)=O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCC(OC)OC>>COC(CCN1C(NC(C(=C1)C1=NC=CN=C1)=O)=O)OC | Br[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:20][CH3:21].[nH:6]1[cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[c:15](=[O:16])[nH:17][c:18]1=[O:19])[O:20][CH3:21] | COC(CCBr)OC.O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | 35 | [{"value": 35.0, "product": "COC(CCN1C(NC(C(=C1)C1=NC=CN=C1)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "COC(CCN1C(NC(C(=C1)C1=NC=CN=C1)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 5-pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep125, 2.19 mmol), and K2CO3 (302 mg, 2.19 mmol) in DMF (20 ml) was stirred 30 minutes at room temperature. 90% 3-Bromo-1,1dimethoxy-propane (365 μl, 2.41 mmol) was added in two portions during 2 days. Water was added and the mixture was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cnccn1 | HBr | CN(C)C=O | null | 0.5 | COC(CCBr)OC.O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1>CN(C)C=O>COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-01977344dbf843af8d4b4a50a13b038e | COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC>>O=CCCn1cc(-c2cnccn2)c(=O)[nH]c1=O | COC(CCN1C(NC(C(=C1)C1=NC=CN=C1)=O)=O)OC>>O=C1N(C=C(C(N1)=O)C1=NC=CN=C1)CCC=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][cH:12][n:13]2)[c:14](=[O:15])[nH:16][c:17]1=[O:18]>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][cH:12][n:13]2)[c:14](=[O:15])[nH:16][c:17]1=[O:18] | COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC | O=CCCn1cc(-c2cnccn2)c(=O)[nH]c1=O | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1[nH]cc(-c2cnccn2)c(=O)[nH]1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 40 | CELSIUS | 4 | HOUR | 1-(3,3-Dimethoxy-propyl)-5-pyrazin-2-yl-1H-pyrimidine-2,4-dione (Prep126, 111 mg, 0.38 mmol) was dissolved in THF (4 ml) and then 1N HClaq (0.38 ml) was added. The solution was stirred at 40° C. for 4 hours. TEA (55 μl, 0.39 mmol) was added and the solvent was removed in vacuum at room temperature. Residue was freeze d... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1cncnc1.c1cnccn1 | HO- | C1CCOC1 | 40 | 4 | COC(CCn1cc(-c2cnccn2)c(=O)[nH]c1=O)OC>C1CCOC1>O=CCCn1cc(-c2cnccn2)c(=O)[nH]c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fdbc1d13149b4ffb80399fe7c46b1680 | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1>>O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | IC=1C(NC(NC1)=O)=O.C(C1=CC=CC=C1)(=O)Cl.O>>C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[nH:9]1[c:10](=[O:11])[nH:12][cH:13][c:14]([I:15])[c:16]1=[O:17]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[nH:12][cH:13][c:14]([I:15])[c:16]1=[O:17] | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1 | O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | null | null | N1=CC=CC=C1 | Acylation | N-alkylation of secondary amines with alkyl halides | 424d6b217c72b1bfc74a70456602e1889d454da2579c9467b12c0e5157dbc176 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:1>>[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 90.5 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 5-iodouracil (2 g, 8.4 mmol) in dry pyridine (20 ml) was added dropwise to a solution of benzoyl chloride (3.5 g, 25.3 mmol) in pyridine (10 ml). The mixture was stirred at room temperature for 3 hours. Water (70 ml) was added and extracted with ethyl acetate. The organic phase washed with a saturated sol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | N1=CC=CC=C1 | null | 3 | O=C(Cl)c1ccccc1.O=c1[nH]cc(I)c(=O)[nH]1>N1=CC=CC=C1>O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fc016c9b3fec4379b34ff4bf91e99717 | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | BrCCCCCl.C(C1=CC=CC=C1)(=O)N1C(NC=C(C1=O)I)=O.C(=O)([O-])[O-].[K+].[K+].O.BrCCCCCl>>C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O | Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][nH:15][c:21]1=[O:22]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[n:9]1[c:10](=[O:11])[c:12]([I:13])[cH:14][n:15]([CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])[c:21]1=[O:22] | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O | O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ee0dcde5329eb85ca4e92153764f891e6c938eacaaefd406799e322c916af651 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(c1ccccc1)n1c(=O)cc[nH]c1=O | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1=[O;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6](-[C:5]=[O;D1;H0:4]):[c:11]:1=[O;D1;H0:12] | 98 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "C(C1=CC=CC=C1)(=O)N1C(N(C=C(C1=O)I)CCCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep128, 2.5 g, 7.3 mmol), K2CO3 (1 g, 7.3 mmol) and 1-bromo-4-chloro-butane (1.26 ml, 10.95 mmol) were suspended in dry DMF (10 ml). After stirring the reaction at room temperature overnight, further 1-bromo-4-chloro-butane (840 μl, 7.3 mmol) was added. Water was added and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HBr | CN(C)C=O | null | null | ClCCCCBr.O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O>CN(C)C=O>O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O |
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