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-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac255e6bb40c46cda441168046b3c284 | CCN1C=C[CH-]B1c1ccccc1.[Cl-].[Zr+4]>>CCN1C=C[CH]([Zr+2][CH]2C=CN(CC)B2c2ccccc2)B1c1ccccc1.[Cl-] | C(C)N1B([CH-]C=C1)C1=CC=CC=C1.[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>>[Cl-].[Cl-].C(C)N1B(C(C=C1)[Zr+2]C1B(N(C=C1)CC)C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][N:3]1[CH:4]=[CH:5][CH-:6][B:14]1[c:15]1[cH:16][cH:8][cH:18][cH:19][cH:20]1.[Cl-:28].[Zr+4:7]>>[CH3:1][CH2:2][N:3]1[CH:4]=[CH:5][CH:6]([Zr+2:7][CH:8]2[CH:9]=[CH:10][N:11]([CH2:12][CH3:13])[B:14]2[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[B:21]1[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[Cl-:28] | CCN1C=C[CH-]B1c1ccccc1.[Cl-].[Zr+4] | CCN1C=C[CH]([Zr+2][CH]2C=CN(CC)B2c2ccccc2)B1c1ccccc1.[Cl-] | null | null | CCOCC | Aromatic Heterocycle Formation | OtherReaction | a9ba1af8844c8faccb7d58662c124ed358bb81500a004b1aacc236de966216f0 | eeac1b4bd6e787ffd442046a21dde8ec65883eca0c18a3b2257563c102485f41 | C1=C[CH]([Zr+2][CH]2C=CNB2c2ccccc2)B(c2ccccc2)N1 | [C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4]=[C:5]-[CH-;D2:6]-[B;H0;D3;+0:7]-1-[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[Zr+4;H0;D0:14]>>[C:15]-[#7:16]1-[C:17]=[C:18]-[CH;D3;+0:12](-[Zr+2;H0;D2:14]-[CH;D3;+0:6]2-[C:5]=[C:4]-[N;H0;D3;+0:3](-[C:2]-[C;D1;H3:1])-[#5:19]-2-[c:20])-[B;H0;D3;+0:7]-1-[c:8]1:[... | 59 | [{"value": 59.0, "product": "[Cl-].[Cl-].C(C)N1B(C(C=C1)[Zr+2]C1B(N(C=C1)CC)C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 8 | HOUR | A suspension of lithium (1-ethyl-2-phenyl-1,2-azaborolide) (1C), 0.80 g, 4.52 mmol) in 25 mL of ether was added to a suspension of ZrCl4 (0.51 g, 2.19 mmol) in 25 mL of ether at −50° C. The mixture was stirred for 8 h, during which time the mixture warmed to 25° C. The mixture was filtered through diatomaceous earth an... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Enamine.Enamine | [B]1[CH-]C=C[NH]1.c1ccccc1 | [B]1CC=C[NH]1.[B]1CC=C[NH]1.c1ccccc1.c1ccccc1 | [B]1CC=C[NH]1.[B]1CC=C[NH]1.c1ccccc1.c1ccccc1 | null | CCOCC | 25 | 8 | CCN1C=C[CH-]B1c1ccccc1.[Cl-].[Zr+4]>CCOCC>CCN1C=C[CH]([Zr+2][CH]2C=CN(CC)B2c2ccccc2)B1c1ccccc1.[Cl-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-637bc45e13214786913531fb8612dc35 | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.[Li][CH]1C=CC=C1>>CCN1C=CC([Si](C)(C)C2C=CC=C2)B1c1ccccc1 | C1(C=CC=C1)[Li].C(C)N1B(C(C=C1)(Cl)[SiH](C)C)C1=CC=CC=C1>>C(C)N1B(C(C=C1)[Si](C)(C)C1C=CC=C1)C1=CC=CC=C1 | Cl[C:6]1([SiH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]([CH2:2][CH3:1])[B:15]1[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[Li][CH:10]1[CH:11]=[CH:12][CH:13]=[CH:14]1>>[CH3:1][CH2:2][N:3]1[CH:4]=[CH:5][CH:6]([Si:7]([CH3:8])([CH3:9])[CH:10]2[CH:11]=[CH:12][CH:13]=[CH:14]2)[B:15]1[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.[Li][CH]1C=CC=C1 | CCN1C=CC([Si](C)(C)C2C=CC=C2)B1c1ccccc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 967d44ade25c243e23ca48a02b71b6135a22ba815c9c7a6b4161b79c93f2c728 | b44fe623847ebb480a32c472af03abea80d165483457ffbaf9ebebad2ed0a1cf | C1=CC([SiH2]C2C=CNB2c2ccccc2)C=C1 | Cl-[C;H0;D4;+0:1]1(-[SiH;D3;+0:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:5]=[C:6]-[#7:7]-[#5:8]-1-[c:9].[Li]-[CH;D3;+0:10]1-[C:11]=[C:12]-[C:13]=[C:14]-1>>[C;D1;H3:3]-[Si;H0;D4;+0:2](-[C;D1;H3:4])(-[CH;D3;+0:10]1-[C:11]=[C:12]-[C:13]=[C:14]-1)-[CH;D3;+0:1]1-[C:5]=[C:6]-[#7:7]-[#5:8]-1-[c:9] | 87.1 | [{"value": 87.0, "product": "C(C)N1B(C(C=C1)[Si](C)(C)C1C=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "C(C)N1B(C(C=C1)[Si](C)(C)C1C=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 12 | HOUR | A solution of cyclopentadienyl lithium (0.16 g, 2.27 mmol) in 10 mL of THF was added slowly to a solution of 1-ethyl-3-chlorodimethylsilyl-2,3-dihydro-2-phenyl-1H-1,2-azaborole (0.60 g, 2.27 mmol) in 10 mL of THF at −50° C. The reaction mixture wag slowly warmed to 25° C. and stirred for 12 h. The solvent was removed i... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Alkyl lithium | Silyl protective group | [B]1CC=C[NH]1.C1=CCC=C1 | [B]1CC=C[NH]1.C1=CCC=C1 | [B]1CC=C[NH]1.C1=CCC=C1.c1ccccc1 | Li | C1CCOC1 | 25 | 12 | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.[Li][CH]1C=CC=C1>C1CCOC1>CCN1C=CC([Si](C)(C)C2C=CC=C2)B1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3f8133feaf8461ea6858c5468e3a30a | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.CCN1C=C[CH-]B1c1ccccc1>>CCN1C=CC([Si](C)(C)C2C=CN(CC)B2c2ccccc2)B1c1ccccc1 | C(C)N1B([CH-]C=C1)C1=CC=CC=C1.[Li+].C(C)N1B(C(C=C1)(Cl)[SiH](C)C)C1=CC=CC=C1>>C(C)N1B(C(C=C1)[Si](C)(C)C1B(N(C=C1)CC)C1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:6]1([SiH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]([CH2:2][CH3:1])[B:23]1[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[CH-:10]1[CH:11]=[CH:12][N:13]([CH2:14][CH3:15])[B:16]1[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][N:3]1[CH:4]=[CH:5][CH:6]([Si:7]([CH3:8])([CH3:9])[CH:10]2[CH:11]=[CH:12][N:13]([CH2:14]... | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.CCN1C=C[CH-]B1c1ccccc1 | CCN1C=CC([Si](C)(C)C2C=CN(CC)B2c2ccccc2)B1c1ccccc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 2384d40889d710b512c841b76d1d27db5440450a70c5bc93469e7d3ee9af3bb2 | 48c4ce3515972fdafe37de91e484911c5d90b12b5eb4d8e839bf03b8d1006043 | C1=CC([SiH2]C2C=CNB2c2ccccc2)B(c2ccccc2)N1 | Cl-[C;H0;D4;+0:1]1(-[SiH;D3;+0:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:5]=[C:6]-[#7:7]-[#5:8]-1-[c:9].[c:10]-[#5:11]1-[#7:12]-[C:13]=[C:14]-[CH-;D2:15]-1>>[C;D1;H3:3]-[Si;H0;D4;+0:2](-[C;D1;H3:4])(-[CH;D3;+0:15]1-[C:14]=[C:13]-[#7:12]-[#5:11]-1-[c:10])-[CH;D3;+0:1]1-[C:5]=[C:6]-[#7:7]-[#5:8]-1-[c:9] | 92 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared in the same manner as Example 3B) from lithium (1-ethyl-2-phenyl-1,2-azaborolide) (1C), 0.41 g, 2.31 mmol) in 15 mL of THF and 1-ethyl-3-chlorodimethylsilyl-2,3-dihydro-2-phenyl-1H-1,2-azaborole (Ex. 3A), 0.01 g, 2.31 mmol) in 15 mL of THF. The product was obtained as a yellow oil (0.85 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | Silyl protective group | [B]1CC=C[NH]1.[B]1[CH-]C=C[NH]1 | [B]1CC=C[NH]1.[B]1CC=C[NH]1 | [B]1CC=C[NH]1.[B]1CC=C[NH]1.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | CCN1C=CC(Cl)([SiH](C)C)B1c1ccccc1.CCN1C=C[CH-]B1c1ccccc1>C1CCOC1>CCN1C=CC([Si](C)(C)C2C=CN(CC)B2c2ccccc2)B1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-976d026fc2624c0ab091f731d189ba3f | C=CCNCC=C.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.ClB(Cl)Cl>>C=CCB(Cl)N(CC=C)CC=C | C(C)N(CC)CC.C(C=C)[Sn](CCCC)(CCCC)CCCC.B(Cl)(Cl)Cl.C(C=C)NCC=C>>C(C=C)B(N(CC=C)CC=C)Cl | [NH:6]([CH2:7][CH:8]=[CH2:9])[CH2:10][CH:11]=[CH2:12].CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:3][CH:2]=[CH2:1].Cl[B:4](Cl)[Cl:5]>>[CH2:1]=[CH:2][CH2:3][B:4]([Cl:5])[N:6]([CH2:7][CH:8]=[CH2:9])[CH2:10][CH:11]=[CH2:12] | C=CCNCC=C.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.ClB(Cl)Cl | C=CCB(Cl)N(CC=C)CC=C | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 18b28536264228886eb3b482441696f1859d58eb1c6468c8df829a85968abea6 | e5bac67a68df2b4f2ce4b0d59d1b75c869953022d4730d21a0e7abe2a3b2459b | null | C-C-C-[CH2]-[Sn](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])(-[CH2]-C-C-C)-[CH2]-C-C-C.Cl-[B;H0;D3;+0:4](-Cl)-[Cl;D1;H0:5].[C;D1;H2:6]=[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]=[C;D1;H2:12]>>[C;D1;H2:6]=[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11]=[C;D1;H2:12])-[B;H0;D3;+0:4](-[Cl;D1;H0:5])-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | 95 | [{"value": 95.0, "product": "C(C=C)B(N(CC=C)CC=C)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "C(C=C)B(N(CC=C)CC=C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | A solution of allyltributyltin (62.2 g, 0.19 mol) in 50 mL of hexane was added dropwise to a solution of BCl3 (24.8 g, 0.21 mol) in 120 mL of hexane at −78° C. After the reaction mixture was stirred at −78° C. for 1 hour, it was allowed to warm to 25° C. for 2 hours followed by recooling to −78° C. Then diallylamine (2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Allyl.Tin | Tertiary amine.Allyl | null | null | null | HCl.Sn | CCCCCC | -78 | 1 | C=CCNCC=C.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.ClB(Cl)Cl>CCCCCC>C=CCB(Cl)N(CC=C)CC=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e898694a01e844708cdf96569ef0e5ce | C=CCCCCCC>>C=CCCCCCC | C[Al]1OCCCC1.C=CCCCCCC.[H][H].C=C.C=C>>C=C.C=CCCCCCC | [CH2:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>>[CH2:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10] | C=CCCCCCC | C=CCCCCCC | null | null | CCCCCC.C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | All liquid and gas feeds were passed through columns of alumina and a decontaminant (Q-5™ catalyst available from Englehardt Chemicals Inc.) prior to introduction into the reactor. Catalyst components are handled in a glovebox containing an atmosphere of argon or nitrogen. A stirred 2.0 liter reactor is charged with 74... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCCCCC.C1(=CC=CC=C1)C | null | null | C=CCCCCCC>CCCCCC.C1(=CC=CC=C1)C>C=CCCCCCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-945787f8cf174b1f88143a1b23cae68b | CCOC([O-])[O-].Cc1ccc(S(=O)(=O)O)cc1.O=CC1(C=O)CC1>>CCOC(OCC)C1(C=O)CC1 | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(CC1)(C=O)C=O.[OH-].[Na+].C(OCC)([O-])[O-]>>C(C)OC(C1(CC1)C=O)OCC | [O-][CH:4]([O-:3])[O:5][CH2:6][CH3:7].Cc1ccc(S(=O)(=O)O)[cH:1][cH:2]1.O=C[C:8]1([CH:9]=[O:10])[CH2:11][CH2:12]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([CH:9]=[O:10])[CH2:11][CH2:12]1 | CCOC([O-])[O-].Cc1ccc(S(=O)(=O)O)cc1.O=CC1(C=O)CC1 | CCOC(OCC)C1(C=O)CC1 | null | null | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | b498c200f9a727ceccbd57c8183d07f0b333c0272a95f73b7fd320947d887346 | 39e9b18af34ed7b3d00ec4f31a8bc70339fd251823aad56bf279b69ab5b3c4dd | C1CC1 | C-c1:[cH;D2;+0:1]:[cH;D2;+0:2]:c(-S(-O)(=O)=O):c:c:1.O=C-[C;H0;D4;+0:3]1(-[C:4]=[O;D1;H0:5])-[C:6]-[C:7]-1.[C:8]-[#8:9]-[CH;D3;+0:10](-[O-;H0;D1:11])-[O-]>>[C:8]-[#8:9]-[CH;D3;+0:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[CH3;D1;+0:2])-[C;H0;D4;+0:3]1(-[C:4]=[O;D1;H0:5])-[C:6]-[C:7]-1 | null | [] | 20 | CELSIUS | 1 | HOUR | In toluene (260 ml) was dissolved 1,1-cyclopropane dicarboaldehyde (30 g, 306 mmol). The resulting solution was stirred at 20° C. To the reaction mixture was added dropwise a solution of p-toluenesulfonate monohydrate (153 mg, 0.77 mml) in toluene (10 ml) and the mixture was cooled to the internal temperature of 5° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Aldehyde.Ether | Aldehyde.Ether.Ether | c1ccccc1.C1CC1 | C1CC1 | C1CC1 | TsOH.HO- | O.C1(=CC=CC=C1)C | 20 | 1 | CCOC([O-])[O-].Cc1ccc(S(=O)(=O)O)cc1.O=CC1(C=O)CC1>O.C1(=CC=CC=C1)C>CCOC(OCC)C1(C=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d4978a87be3401ca1a50f6435b78c9c | CCO.CCOC([O-])[O-].NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N>>CCOC(OCC)C1(C(C#N)NCc2ccccc2)CC1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)N.[C-]#N.[K+].S([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].C(C)O.C(OCC)([O-])[O-].C1(CC1)(C=O)C=O>>C(C1=CC=CC=C1)NC(C#N)C1(CC1)C(OCC)OCC | [CH3:1][CH2:2][OH:3].[O-]C([O-])[O:5][CH2:6][CH3:7].[NH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=[CH:4][C:8]1([CH:9]=O)[CH2:20][CH2:21]1.[C-:10]#[N:11]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([CH:9]([C:10]#[N:11])[NH:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | CCO.CCOC([O-])[O-].NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N | CCOC(OCC)C1(C(C#N)NCc2ccccc2)CC1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 13d810ec3e5258ea882ddfb2ea145dd1c02295a3ebb9435e2b2a31b962934eb4 | 84690ce887e7c82e0f18a8300217841d1f03f0db372e630643ad82032eb9b1c2 | c1ccc(CNCC2CC2)cc1 | O=[CH;D2;+0:1]-[C:2]1(-[CH;D2;+0:3]=O)-[C:4]-[C:5]-1.[C-;H0;D1:6]#[N;D1;H0:7].[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-C(-[O-])-[O-].[C;D1;H3:11]-[C:12]-[OH;D1;+0:13].[NH2;D1;+0:14]-[C:15]-[c:16]>>[C;D1;H3:11]-[C:12]-[O;H0;D2;+0:13]-[CH;D3;+0:1](-[O;H0;D2;+0:10]-[C:9]-[C;D1;H3:8])-[C:2]1(-[CH;D3;+0:3](-[C;H0;D2;+0:6]#[N;D1;H0... | 712 | [{"value": 71.2, "product": "C(C1=CC=CC=C1)NC(C#N)C1(CC1)C(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 712.0, "product": "C(C1=CC=CC=C1)NC(C#N)C1(CC1)C(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In toluene (30 ml) was dissolved 1,1-cyclopropane dicarboaldehyde (2.94 g, 30 mmol). Under ice cooling and stirring, a solution of p-toluenesulfonate monohydrate (5.7 mg, 0.03 mmol) in ethanol (138 mg, 3.0 mmol), and then, ethyl orthoformate (4.67 g, 31.5 mmol) were added. The resulting mixture was stirred at the exter... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Primary alcohol.Primary amine | Ether.Ether.Nitrile.Secondary amine | null | null | c1ccccc1.C1CC1 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | CCO.CCOC([O-])[O-].NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC>CCOC(OCC)C1(C(C#N)NCc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-843bcf725c3343649b5e49e24eb1996e | CCO.CCOC([O-])[O-].C[C@H](N)c1ccccc1.O=CC1(C=O)CC1.[C-]#N>>CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | C([O-])(O)=O.[Na+].C1(=CC=CC=C1)[C@H](C)N.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)O.C(OCC)([O-])[O-].[C-]#N.[K+].C1(CC1)(C=O)C=O.C([O-])(O)=O.[Na+].S([O-])(O)=O.[Na+]>>C(C)OC(C1(CC1)[C@@H](C#N)N[C@@H](C)C1=CC=CC=C1)OCC | [CH3:1][CH2:2][OH:3].[O-]C([O-])[O:5][CH2:6][CH3:7].[NH2:12][C@@H:13]([CH3:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.O=[CH:4][C:8]1([CH:9]=O)[CH2:21][CH2:22]1.[C-:10]#[N:11]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@@H:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c... | CCO.CCOC([O-])[O-].C[C@H](N)c1ccccc1.O=CC1(C=O)CC1.[C-]#N | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | null | null | O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 13d810ec3e5258ea882ddfb2ea145dd1c02295a3ebb9435e2b2a31b962934eb4 | 84690ce887e7c82e0f18a8300217841d1f03f0db372e630643ad82032eb9b1c2 | c1ccc(CNCC2CC2)cc1 | O=[CH;D2;+0:1]-[C:2]1(-[CH;D2;+0:3]=O)-[C:4]-[C:5]-1.[C-;H0;D1:6]#[N;D1;H0:7].[C;D1;H3:8]-[C:9](-[NH2;D1;+0:10])-[c:11].[C;D1;H3:12]-[C:13]-[O;H0;D2;+0:14]-C(-[O-])-[O-].[C;D1;H3:15]-[C:16]-[OH;D1;+0:17]>>[C;D1;H3:8]-[C:9](-[c:11])-[NH;D2;+0:10]-[C@H;D3;+0:3](-[C;H0;D2;+0:6]#[N;D1;H0:7])-[C:2]1(-[CH;D3;+0:1](-[O;H0;D2;... | null | [] | null | null | 30 | MINUTE | In toluene (20 ml) was dissolved 1,1-cyclopropane dicarboaldehyde (1.96 g, 20 mmol). Under ice cooling and stirring, a solution of p-toluenesulfonate monohydrate (19.2 mg, 0.1 mmol) in ethanol (276 mg, 6.0 mmol), and then ethyl orthoformate (3.11 g, 21 mmol) were added. The mixture was stirred at the external temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Primary alcohol.Primary amine | Ether.Ether.Nitrile.Secondary amine | null | null | c1ccccc1.C1CC1 | HO- | O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | 0.5 | CCO.CCOC([O-])[O-].C[C@H](N)c1ccccc1.O=CC1(C=O)CC1.[C-]#N>O.CCCCCC.C1(=CC=CC=C1)C.C(C)(=O)OCC>CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f476147ba0b47b4ae3fc8316ab86d5d | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1>>CCOC(OCC)C1([C@H](C#N)N[C@@H](C)c2ccccc2)CC1 | C(C)OC(C1(CC1)[C@@H](C#N)N[C@@H](C)C1=CC=CC=C1)OCC>>C(C)OC(C1(CC1)[C@H](C#N)N[C@@H](C)C1=CC=CC=C1)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@@H:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@H:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][C... | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | CCOC(OCC)C1([C@H](C#N)N[C@@H](C)c2ccccc2)CC1 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(CNCC2CC2)cc1 | null | null | [] | null | null | null | null | Anhydrous ethanol (1.0 ml) was added to a mixture of the title compound and its diastereomer, (2S)-2-[1-(diethoxymethyl)cyclopropyl]-2-{[(1S)-1-phenylethyl]amino}acetonitrile (the mixture: 16 mg, mixing ratio=1:1.8, (2S)-2-[1-(diethoxymethyl)cyclopropyl]-2-{[(1S)-1-phenylethyl]amino}acetonitrile was a main component). ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CC1 | null | C(C)O | null | null | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1>C(C)O>CCOC(OCC)C1([C@H](C#N)N[C@@H](C)c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8d526ce1ebf43a795ddc514a8c2c217 | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1>>CCOC(OCC)C1([C@@H](CN)N[C@@H](C)c2ccccc2)CC1 | [H][H].C(C)OC(C1(CC1)[C@@H](C#N)N[C@@H](C)C1=CC=CC=C1)OCC.[OH-].[Na+]>>NC[C@H](C1(CC1)C(OCC)OCC)N[C@@H](C)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@@H:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@@H:9]([CH2:10][NH2:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:2... | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | CCOC(OCC)C1([C@@H](CN)N[C@@H](C)c2ccccc2)CC1 | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(CNCC2CC2)cc1 | [#7:1]-[C:2](-[C:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#7:1]-[C:2](-[C:3])-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | In ethanol (9.0 ml) was dissolved (2S)-2-[1-(diethoxymethyl)cyclopropyl]-2-{[(1S)-1-phenylethyl]amino}acetonitrile (150 mg, 0.496 mmol). To the resulting solution were added a 5 mol/l aqueous solution of sodium hydroxide (0.5 ml, 2.5 mmol) and Raney-nickel (R-100, 1.5 g) were added and the mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1CC1 | null | [Ni].C(C)O | null | null | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1>[Ni].C(C)O>CCOC(OCC)C1([C@@H](CN)N[C@@H](C)c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2ffe11e5c51412598898fc7c32ee761 | CCOC(OCC)C1(C=O)CC1>>CCOC(OCC)C1(CO)CC1 | O1CCCC1.C(C)OC(C1(CC1)C=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)OC(C1(CC1)CO)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([CH:9]=[O:10])[CH2:11][CH2:12]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([CH2:9][OH:10])[CH2:11][CH2:12]1 | CCOC(OCC)C1(C=O)CC1 | CCOC(OCC)C1(CO)CC1 | null | null | O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | C1CC1 | [C:1]-[C:2]1(-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5]-[C:6]-1>>[C:1]-[C:2]1(-[CH2;D2;+0:3]-[OH;D1;+0:4])-[C:5]-[C:6]-1 | 91 | [{"value": 91.0, "product": "C(C)OC(C1(CC1)CO)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C(C)OC(C1(CC1)CO)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | A tetrahydrofuran (190 mL) solution of 1-(diethoxymethyl)cyclopropane carboaldehyde (37.78 g) was cooled to 0° C. Lithium aluminum hydride (2 g, 52.7 mmol) was added and the mixture was stirred for 40 minutes. Water was added to terminate the reaction, followed by extraction with chloroform. The organic layer was washe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1CC1 | null | O | null | 0.666667 | CCOC(OCC)C1(C=O)CC1>O>CCOC(OCC)C1(CO)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8fc002d690874d13a0c63471e87da354 | C[C@H](N)c1ccccc1.O=CC1(CO)CC1.[C-]#N>>C[C@H](NC(C#N)C1(CO)CC1)c1ccccc1 | OCC1(CC1)C=O.C1(=CC=CC=C1)[C@H](C)N.[C-]#N.[K+].S([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+]>>OCC1(CC1)C(C#N)N[C@@H](C)C1=CC=CC=C1 | [CH3:1][C@H:2]([NH2:3])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.O=[CH:4][C:7]1([CH2:8][OH:9])[CH2:10][CH2:11]1.[C-:5]#[N:6]>>[CH3:1][C@H:2]([NH:3][CH:4]([C:5]#[N:6])[C:7]1([CH2:8][OH:9])[CH2:10][CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C[C@H](N)c1ccccc1.O=CC1(CO)CC1.[C-]#N | C[C@H](NC(C#N)C1(CO)CC1)c1ccccc1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 67834ce29ee7faed9c771a892a45df3a078cc52972b167e999c188543c3ef065 | 8743950731596ea1e685ccc6d45d1ba830801fe94588e1dd93bbf1291f95e93b | c1ccc(CNCC2CC2)cc1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3])-[C:4]-[C:5]-1.[C-;H0;D1:6]#[N;D1;H0:7].[C;D1;H3:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:3]-[C:2]1(-[CH;D3;+0:1](-[C;H0;D2;+0:6]#[N;D1;H0:7])-[NH;D2;+0:10]-[C:9](-[C;D1;H3:8])-[c:11])-[C:4]-[C:5]-1 | null | [] | 50 | CELSIUS | 30 | MINUTE | To an ethanol (4.9 mL) solution of 1-(hydroxymethyl)cyclopropane carboaldehyde (683 mg, 6.82 mmol) were added water (2.1 mL), (S)-(−)-1-phenylethylamine (0.94 mL, 7.50 mmol), potassium cyanide (489 mg, 7.50 mmol) and sodium bisulfite (1.45 g, 13.6 mmol). The mixture was stirred at 50° C. for 30 minutes. After cooling t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile.Secondary amine | null | null | C1CC1.c1ccccc1 | HO- | O.C(C)O | 50 | 0.5 | C[C@H](N)c1ccccc1.O=CC1(CO)CC1.[C-]#N>O.C(C)O>C[C@H](NC(C#N)C1(CO)CC1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-608867c614f7451cb92cc5962df472bd | NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N>>N#CC(NCc1ccccc1)C1(C=O)CC1 | C([O-])(O)=O.[Na+].S([O-])(O)=O.[Na+].[C-]#N.[K+].C(C1=CC=CC=C1)N.C1(CC1)(C=O)C=O>>C(C1=CC=CC=C1)NC(C#N)C1(CC1)C=O | [NH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.O=[CH:3][C:12]1([CH:13]=[O:14])[CH2:15][CH2:16]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH:3]([NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C:12]1([CH:13]=[O:14])[CH2:15][CH2:16]1 | NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N | N#CC(NCc1ccccc1)C1(C=O)CC1 | null | null | CCCCCC.O.C(C)(=O)OCC.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 67834ce29ee7faed9c771a892a45df3a078cc52972b167e999c188543c3ef065 | 8743950731596ea1e685ccc6d45d1ba830801fe94588e1dd93bbf1291f95e93b | c1ccc(CNCC2CC2)cc1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3]=[O;D1;H0:4])-[C:5]-[C:6]-1.[C-;H0;D1:7]#[N;D1;H0:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[N;D1;H0:8]#[C;H0;D2;+0:7]-[CH;D3;+0:1](-[NH;D2;+0:9]-[C:10]-[c:11])-[C:2]1(-[C:3]=[O;D1;H0:4])-[C:5]-[C:6]-1 | 50.9 | [{"value": 50.8, "product": "C(C1=CC=CC=C1)NC(C#N)C1(CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.9, "product": "C(C1=CC=CC=C1)NC(C#N)C1(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzylamine (107 mg, 1.0 mmol) was suspended in a mixture of ethanol (0.5 ml) and water (1.5 ml). To the resulting suspension were successively added potassium cyanide (65 mg, 1.0 mmol) and sodium bisulfite (104 mg, 1.0 mmol) under ice cooling and stirring. An ethanol (1.5 ml) solution of 1,1-cyclopropane dicarboaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile.Secondary amine | null | null | c1ccccc1.C1CC1 | HO- | CCCCCC.O.C(C)(=O)OCC.C(C)O | null | null | NCc1ccccc1.O=CC1(C=O)CC1.[C-]#N>CCCCCC.O.C(C)(=O)OCC.C(C)O>N#CC(NCc1ccccc1)C1(C=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b67d968e1534cda954c23cbcb1adade | CCOC(OCC)OCC.C[C@H](NC(C#N)C1(C=O)CC1)c1ccccc1>>CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | C([O-])(O)=O.[Na+].C(OCC)(OCC)OCC.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(=O)C1(CC1)C(C#N)N[C@@H](C)C1=CC=CC=C1>>C(C)OC(C1(CC1)[C@@H](C#N)N[C@@H](C)C1=CC=CC=C1)OCC | CCOC(O[CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[O:3]=[CH:4][C:8]1([CH:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]1([C@@H:9]([C:10]#[N:11])[NH:12][C@@H:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2... | CCOC(OCC)OCC.C[C@H](NC(C#N)C1(C=O)CC1)c1ccccc1 | CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | fcd88c7abf874cee525e2d08e112aab4759e77ad93b33f36b8306c7913ea31c2 | 11306b4f2dea9cefbc3d550c8afb389271a44b7cc69c06172e6b191dd38b2284 | c1ccc(CNCC2CC2)cc1 | C-C-O-C(-O-[CH2;D2;+0:1]-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5].[C:6]-[C:7]1(-[CH;D2;+0:8]=[O;H0;D1;+0:9])-[C:10]-[C:11]-1>>[C:6]-[C:7]1(-[CH;D3;+0:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5])-[C:10]-[C:11]-1 | null | [] | null | null | 30 | MINUTE | Triethyl orthoformate (0.2 mL, 1.20 mmol) and p-toluenesulfonate monohydrate (1 mg, 0.0053 mmol) were added to an ethanol (2.5 mL) solution of 2-(1-formylcyclopropyl)-2-{[(1S)-1-phenylethyl]amino}acetonitrile (102 mg, 0.447 mmol). The resulting mixture was stirred at room temperature for 2 hours and 30 minutes and then... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether.Ether | Ether.Ether | null | null | c1ccccc1.C1CC1 | HO- | C(C)O | null | 0.5 | CCOC(OCC)OCC.C[C@H](NC(C#N)C1(C=O)CC1)c1ccccc1>C(C)O>CCOC(OCC)C1([C@@H](C#N)N[C@@H](C)c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d204c784d7e4f83b4c066cf9886e97e | CO[Si](CCCSC(C)=O)(OC)OC>>CCC(=O)SCCC[Si](OC)(OC)OC | SCCC[Si](OC)(OC)OC.CSCCC[Si](OC)(OC)OC.[Na+].[Cl-].SCCC[Si](OC)(OC)OC.C[O-].[Na+].C(C)(=O)SCCC[Si](OC)(OC)OC.C[O-].[Na+]>>C(CC)(=O)SCCC[Si](OC)(OC)OC | [CH3:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15]>>[CH3:1][CH2:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15] | CO[Si](CCCSC(C)=O)(OC)OC | CCC(=O)SCCC[Si](OC)(OC)OC | null | null | C1(=CC=CC=C1)C | Miscellaneous | Methylation | 6c60a9cd65097a25ff428f775d481db4c10e3c53e07ccd584b19300ed77d7f30 | 6fca8ee80f3da8b18e15687d90afe45d5380c3d17d460e62b59adecbfd8cae6a | null | [#16:1]-[C:2](-[CH3;D1;+0:3])=[O;D1;H0:4]>>[#16:1]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:3]-[C;D1;H3:5] | null | [] | null | null | null | null | 816 grams of 3-mercapto-1-propyltrimethoxysilane, 871 grams of 25 weight percent methanolic solution of sodium methoxide, and 1,724 grams of toluene were charged to a 5-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. Methanol was removed from the flask by distilling off a met... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Carbo-thioester | null | null | null | Other | C1(=CC=CC=C1)C | null | null | CO[Si](CCCSC(C)=O)(OC)OC>C1(=CC=CC=C1)C>CCC(=O)SCCC[Si](OC)(OC)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86dbbedafea143d19fc3339faf12ba20 | CCC(=O)Cl.CO[Si](CCCS)(OC)OC>>CCC(=O)SCCC[Si](OC)(OC)OC | C(CC)(=O)Cl.[Na+].[Cl-].SCCC[Si](OC)(OC)OC.SCCC[Si](OC)(OC)OC.C[O-].[Na+].CSCCC[Si](OC)(OC)OC.C(C)(=O)SCCC[Si](OC)(OC)OC.C[O-].[Na+]>>C(CC)(=O)SCCC[Si](OC)(OC)OC | Cl[C:3]([CH2:2][CH3:1])=[O:4].[SH:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15]>>[CH3:1][CH2:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15] | CCC(=O)Cl.CO[Si](CCCS)(OC)OC | CCC(=O)SCCC[Si](OC)(OC)OC | null | null | C1(=CC=CC=C1)C | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4] | null | [] | null | null | null | null | 1,035 grams of 3-mercapto-1-propyltrimethoxysilane, 1,096 grams of a 25 weight percent methanolic solution of sodium methoxide, and 1,764 grams of toluene were charged to a S-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. The flask was placed into a water bath at 64° C. Meth... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | null | HCl | C1(=CC=CC=C1)C | null | null | CCC(=O)Cl.CO[Si](CCCS)(OC)OC>C1(=CC=CC=C1)C>CCC(=O)SCCC[Si](OC)(OC)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-748a6ac4a2df4bbb984c77f6881196ee | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | C(CCCCCCC)(=O)Cl.N#N.SCCC[Si](OCC)(OCC)OCC.[SiH4]>>C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[S:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20... | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC | CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | null | null | CCCCCC.C(C)N(CC)CC | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 87 | [{"value": 87.0, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Crompton Corp. of Greenw... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | null | HCl | CCCCCC.C(C)N(CC)CC | null | null | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>CCCCCC.C(C)N(CC)CC>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1b64c68beb64d8bbf9c0095bcbfd990 | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CCCSC(C)=O)(OCC)OCC | S1C(=CC=C1)CC(=O)O.[O-]CC.[Na+].ClCCC[Si](OCC)(OCC)OCC>>C(C)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[CH2:7][CH2:6][CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17].O[C:9]([CH2:10]c1ccc[s:8]1)=[O:11]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][CH2:6][CH2:7][S:8][C:9]([CH3:10])=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17] | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CCCSC(C)=O)(OCC)OCC | null | null | S1C(=CC=C1)C(=O)O.C(C)O | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-c1:[s;H0;D2;+0:7]:c:c:c:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C;H0;D3;+0:4](-[CH3;D1;+0:6])=[O;D1;H0:5] | 78 | [{"value": 78.0, "product": "C(C)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using as a solvent the alcohol corresponding to the silane alkoxy group. Into a 250 ml, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller, heating mantle, addition... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | S1C(=CC=C1)C(=O)O.C(C)O | null | null | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>S1C(=CC=C1)C(=O)O.C(C)O>CCO[Si](CCCSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0615dc57bce24f0a918e0821de51db42 | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CSC(C)=O)(OCC)OCC | S1C(=CC=C1)CC(=O)O.[O-]CC.[Na+].S1C(=CC=C1)C(=O)O.ClC[Si](OCC)(OCC)OCC>>C(C)(=O)SC[Si](OCC)(OCC)OCC | Cl[CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15].O[C:7]([CH2:8]c1ccc[s:6]1)=[O:9]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][S:6][C:7]([CH3:8])=[O:9])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15] | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CSC(C)=O)(OCC)OCC | null | null | COCCOCCOC | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[#14:2](-[#8:3]-[C:4]-[C;D1;H3:5])(-[#8:6]-[C:7]-[C;D1;H3:8])-[#8:9]-[C:10]-[C;D1;H3:11].O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-c1:[s;H0;D2;+0:15]:c:c:c:1>>[C;D1;H3:5]-[C:4]-[#8:3]-[#14:2](-[#8:6]-[C:7]-[C;D1;H3:8])(-[#8:9]-[C:10]-[C;D1;H3:11])-[CH2;D2;+0:1]-[S;H0;D2;+0:15]-[C;H0;D3;+0:12](-[C... | 55 | [{"value": 55.0, "product": "C(C)(=O)SC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 8 | CELSIUS | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using a nonprotic solvent. 88 grams of powdered sodium ethoxide and 600 ml diglyme were charged into a one-liter, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | COCCOCCOC | 8 | null | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>COCCOCCOC>CCO[Si](CSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a685cf4acb941ba9742393b1ac2b3b1 | Cl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21 | [N+](=O)(O)[O-].CN1C(NC(C=2NC=NC12)=O)=O.Cl>>ClC1=NC=2N(C(NC(C2N1)=O)=O)C | [ClH:11].[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[nH:9][cH:10][n:12][c:13]12>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[nH:9][c:10]([Cl:11])[n:12][c:13]12 | Cl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21 | null | null | C(C)(=O)O | Functional Group Addition | Chlorination | ee48548385e3746b65c78e34896e40cae5b4e5887d5b68cbc7bf3b78aa27d5a3 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[#7;a:7]:[cH;D2;+0:8]:[#7;a:9]:[c:10]:1:2.[ClH;D0;+0:11]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[#7;a:7]:[c;H0;D3;+0:8](-[Cl;H0;D1;+0:11]):[#7;a:9]:[c:10]:1:2 | null | [] | 100 | CELSIUS | 30 | MINUTE | Nitric acid (9 ml) was slowly added dropwise to a suspension of 3-methylxanthine (10 g) in acetic acid (180 ml) at 100° C., and the resulting white suspension was stirred at 100° C. for 30 minutes followed by 140° C. for 20 minutes. After cooling the reaction solution to room temperature, the solvent was removed by dis... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | null | C(C)(=O)O | 100 | 0.5 | Cl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>C(C)(=O)O>Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eba40e1b03a04e9bac81fafb421d9fb6 | C=CCBr.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21>>C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C | ClC1=NC=2N(C(NC(C2N1)=O)=O)C.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl | Br[CH2:3][CH:2]=[CH2:1].[nH:4]1[c:5]([Cl:6])[n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16]>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([Cl:6])[n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16] | C=CCBr.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21 | C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 573593e0646e8da604e6bfac1187c2857ed7a59b8b40ccfda36090f9881d8a4d | 4c606dc54eac846ef90c7b3255999ceff93277747e7c2b0ddd37ccf25562b7c5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[nH;D2;+0:11]:[c:12](-[Cl;D1;H0:13]):[#7;a:14]:[c:15]:1:2>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:12](-[Cl;D1;H0:13]):[#7;a:14]:[c:15]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]:2:1 | null | [] | null | null | 17 | HOUR | 8-Chloro-3-methyl-3,7-dihydropurine-2,6-dione (868 mg) and potassium carbonate (628 mg) were suspended in N,N-dimethylformamide (10 ml), and allyl bromide was added dropwise thereto while cooling on ice. After stirring the reaction mixture at room temperature for 17 hours, the resulting white suspension was diluted wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | O.CN(C=O)C.C(C)(=O)OCC | null | 17 | C=CCBr.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21>O.CN(C=O)C.C(C)(=O)OCC>C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe2627da744e42ff93e2a98350f4dbfe | C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | C(C=C)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC=C)=O)=O)C | Cl[c:5]1[n:4]([CH2:3][CH:2]=[CH2:1])[c:21]2[c:20]([n:19]1)[n:27]([CH3:28])[c:25](=[O:26])[nH:24][c:22]2=[O:23].[NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[... | C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1 | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]=[C;D1;H2:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]=[C;D1;H2:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 85.7 | [{"value": 85.7, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC=C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Allyl-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione (420 mg) and 1-piperazine carboxylic acid tert-butyl ester (975 mg) were stirred at 150° C. for 50 minutes. After cooling to room temperature, the resulting reaction mixture was purified by silica gel column chromatography to obtain 584 mg of the title compound from... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | null | null | null | C=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af7ad205287341fbbed303d22e378a13 | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C>>C=CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2C | FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC=C)=O)=O)C>>C(C=C)N1C(=NC=2N(C(NC(C12)=O)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[n:4]([CH2:3][CH:2]=[CH2:1])[c:14]3[c:13]([n:12]2)[n:20]([CH3:21])[c:18](=[O:19])[nH:17][c:15]3=[O:16])[CH2:11][CH2:10]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[n:12][c:13]2[c:14]1[c:15](=[O:16])[nH:17][c:18](=[O:19])[n:20]2[CH3:21] | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | C=CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2C | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 76.2 | [{"value": 76.2, "product": "C(C=C)N1C(=NC=2N(C(NC(C12)=O)=O)C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Trifluoroacetic acid (294 μl) was added dropwise to a solution of 4-(7-allyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (150 mg) in methylene chloride (2 ml), and the reaction mixture was stirred at room temperature for 1 hour and 30 minutes. The solvent was remove... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | C(Cl)Cl | null | 0.5 | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C>C(Cl)Cl>C=CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b8d5e54a691445ab4e1ac037bfb07b4 | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C>>CC(C)=CCn1c(N2CCCNCC2)nc2c1c(=O)[nH]c(=O)n2C | ClC1=NC=2N(C(NC(C2N1CC=C(C)C)=O)=O)C.C(C)(C)(C)OC(=O)N1CCNCCC1.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.N1(CCNCCC1)C1=NC=2N(C(NC(C2N1CC=C(C)C)=O)=O)C | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:14][CH2:13]1.Cl[c:7]1[n:6]([CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[c:17]2[c:16]([n:15]1)[n:23]([CH3:24])[c:21](=[O:22])[nH:20][c:18]2=[O:19]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][n:6]1[c:7]([N:8]2[CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[n:15][c:16]2[c:17]1[c:18... | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C | CC(C)=CCn1c(N2CCCNCC2)nc2c1c(=O)[nH]c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a1d54c008d59c5cb873fef77205fdabcf38524f51c2066eba5fd1159a81173ad | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | O=c1[nH]c(=O)c2[nH]c(N3CCCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10](:[#7;a:11]):[c:12](:[c:13]:[#7;a:14]):[#7;a:15]:1-[C:16]-[C:17]=[C:18]>>[#7;a:14]:[c:13]:[c:12]1:[#7;a:15](-[C:16]-[C:17]=[C:18]):[c;H0;D3;+0:8](-[N;H0;D3;+0:5]2-[C:6]-[C:7]-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]... | null | [] | null | null | 30 | MINUTE | 8-Chloro-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione (40 mg) and 1-homopiperazine carboxylic acid tert-butyl ester (87 μl) were stirred at 140° C. for 1 hour, then trifluoroacetic acid (0.5 ml) was added thereto, and the reaction mixture was stirred at room temperature for 30 minutes. After removing the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | C1C[NH]CCNC1.c1ncc2[nH]cnc2n1 | C1C[NH]CCNC1.c1ncc2[nH]cnc2n1 | C1C[NH]CCNC1.c1ncc2[nH]cnc2n1 | HCl | null | null | 0.5 | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C>>CC(C)=CCn1c(N2CCCNCC2)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13ba33f836d54cd4a64ddcc47e367714 | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CI>>CCOC(=O)Cn1c(=O)c2c(nc(N3CCCNCC3)n2CC=C(C)C)n(C)c1=O | ClC1=NC=2N(C(NC(C2N1CC=C(C)C)=O)=O)C.C(C)(C)(C)OC(=O)N1CCNCCC1.ICC(=O)OCC.FC(C(=O)O)(F)F.C([O-])([O-])=O.[K+].[K+]>>FC(C(=O)O)(F)F.C(C)OC(CN1C(N(C=2N=C(N(C2C1=O)CC=C(C)C)N1CCNCCC1)C)=O)=O | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:20][CH2:19]1.Cl[c:13]1[n:12][c:11]2[c:10]([c:8](=[O:9])[nH:7][c:29](=[O:30])[n:27]2[CH3:28])[n:21]1[CH2:22][CH:23]=[C:24]([CH3:25])[CH3:26].I[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[c:10]2[c:11]([n:12][c:... | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CI | CCOC(=O)Cn1c(=O)c2c(nc(N3CCCNCC3)n2CC=C(C)C)n(C)c1=O | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 754b779bc85c26b5c559b1c1b76e73c840c2dd18ce09e67bab7d9e5a6ac9d189 | cd1b461acc28bda245044e25e49c3ef6d9e3dc7eb355aa8f4567e640600d18dc | O=c1[nH]c(=O)c2[nH]c(N3CCCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:2:[#7;a:19]:1-[C:20]-[C:21]=[C:22].I-[CH2;D2;+0:23]-[C:24](=[O;D1;H0:25])-[#8:26]-[C:27]>>[C:22]=[C:21]-[C:20]-[#... | null | [] | 120 | CELSIUS | 30 | MINUTE | 8-Chloro-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione (100 mg) and potassium carbonate (103 mg) were suspended in N,N-dimethylformamide (2 ml), ethyl iodoacetate (66 μl) was added thereto, and the mixture was stirred at 120° C. for 2 hours and 30 minutes. The reaction mixture was diluted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Ester.Secondary amine.Tertiary amine | C1C[NH]CCNC1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CCNC1 | c1ncc2nc[nH]c2n1.C1C[NH]CCNC1 | HCl.I- | O.CN(C=O)C.C(C)(=O)OCC | 120 | 0.5 | CC(C)(C)OC(=O)N1CCCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CI>O.CN(C=O)C.C(C)(=O)OCC>CCOC(=O)Cn1c(=O)c2c(nc(N3CCCNCC3)n2CC=C(C)C)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8be18deaea584ea4b6ab79b4a47d0b61 | C=CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>>C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C | ClC1=NC=2N(C(N(C(C2N1)=O)C)=O)C.C(C=C)Br.C([O-])([O-])=O.[K+].[K+]>>C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)Cl | Br[CH2:3][CH:2]=[CH2:1].[nH:4]1[c:5]([Cl:6])[n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH3:13])[c:14](=[O:15])[n:16]2[CH3:17]>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([Cl:6])[n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH3:13])[c:14](=[O:15])[n:16]2[CH3:17] | C=CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 573593e0646e8da604e6bfac1187c2857ed7a59b8b40ccfda36090f9881d8a4d | 4c606dc54eac846ef90c7b3255999ceff93277747e7c2b0ddd37ccf25562b7c5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11](-[Cl;D1;H0:12]):[nH;D2;+0:13]:[c:14]:2:[c:15]:1=[O;D1;H0:16]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11](-[Cl;D1;H0:12]):[#7;a:10]:[c:9]2:[#7;a:7](-[C;D1;H3:8]):[c:6]:[#7;a:5](-[C;D1;H3:4]):[c:15](... | null | [] | null | null | 8 | HOUR | A mixture of 8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (10.7 g), allyl bromide (5.2 ml), anhydrous potassium carbonate (10.3 g), and N,N-dimethylformamide (75 ml) was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate and water, and the organic layer was washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C | null | 8 | C=CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>CN(C=O)C>C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c838971beba043dab0973b4dd0a71f71 | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)Cl.C(C)(C)(C)OC(=O)N1CCNCC1.N12CCCCCC2=NCCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C)=O)C)=O)C | Cl[c:5]1[n:4]([CH2:3][CH:2]=[CH2:1])[c:21]2[c:20]([n:19]1)[n:28]([CH3:29])[c:26](=[O:27])[n:24]([CH3:25])[c:22]2=[O:23].[NH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([... | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1 | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]=[C;D1;H2:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]=[C;D1;H2:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 94.4 | [{"value": 94.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | A mixture of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (1.0 g), piperazine-1-carboxylic acid tert-butyl ester (1.1 g), 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (0.59 ml), and 1-methylpyrrolidin-2-one (2 ml) were stirred under nitrogen atmosphere in an oil bath at 140° C. for 2 hours. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | CN1C(CCC1)=O | 140 | 2 | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>CN1C(CCC1)=O>C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd12a9129b4f4a8e9d7fbb561dade17d | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>>C=CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C)=O)C)=O)C.FC(C(=O)O)(F)F>>C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[n:4]([CH2:3][CH:2]=[CH2:1])[c:14]3[c:13]([n:12]2)[n:21]([CH3:22])[c:19](=[O:20])[n:17]([CH3:18])[c:15]3=[O:16])[CH2:11][CH2:10]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[n:12][c:13]2[c:14]1[c:15](=[O:16])[n:17]([CH3:18])[c:19](=[O:20])... | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | C=CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C | null | null | ClCCl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 66.4 | [{"value": 66.4, "product": "C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 4-(7-allyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (1.5 g), trifluoroacetic acid (3 ml), and dichloromethane (10 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. Water (10 ml) and 5 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | ClCCl | null | 3 | C=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>ClCCl>C=CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa8fc4c9e9274884abd572fa6fada0e9 | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.C[C@@H]1CNC[C@H](C)N1>>C=CCn1c(N2CC(C)NC(C)C2)nc2c1c(=O)n(C)c(=O)n2C | C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)Cl.C[C@@H]1N[C@@H](CNC1)C.N12CCCCCC2=NCCC1>>C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CC(NC(C1)C)C | Cl[c:5]1[n:4]([CH2:3][CH:2]=[CH2:1])[c:16]2[c:15]([n:14]1)[n:23]([CH3:24])[c:21](=[O:22])[n:19]([CH3:20])[c:17]2=[O:18].[NH:6]1[CH2:7][C@H:8]([CH3:9])[NH:10][C@H:11]([CH3:12])[CH2:13]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH:8]([CH3:9])[NH:10][CH:11]([CH3:12])[CH2:13]2)[n:14][c:15]2[c:16]1[c:17](=[O:18])[n:1... | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.C[C@@H]1CNC[C@H](C)N1 | C=CCn1c(N2CC(C)NC(C)C2)nc2c1c(=O)n(C)c(=O)n2C | null | null | O.CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a8929f43830cef09a5bff30b4b9aad1a291f1d54cee147bb4d9959b6156f3822 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]=[C;D1;H2:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]=[C;D1;H2:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 42.5 | [{"value": 42.5, "product": "C(C=C)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CC(NC(C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 50 | MINUTE | A suspension of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (200 mg), cis-2,6-dimethylpiperazine (107 mg), and 1,8-diazabicyclo[5.4.0]undec-7-ene (128 μl) in 1-methyl-2-pyrrolidone (2 ml) was stirred at 150° C. for 50 minutes. The reaction mixture was diluted with ethyl acetate and water, and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HCl | O.CN1C(CCC1)=O.C(C)(=O)OCC | 150 | 0.833333 | C=CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.C[C@@H]1CNC[C@H](C)N1>O.CN1C(CCC1)=O.C(C)(=O)OCC>C=CCn1c(N2CC(C)NC(C)C2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-870bb937c10e4e6e91d20464891a1110 | CC#CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>>CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C | ClC1=NC=2N(C(N(C)C(C2N1)=O)=O)C.C([O-])([O-])=O.[K+].[K+].BrCC#CC>>C(C#CC)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)Cl | Br[CH2:4][C:3]#[C:2][CH3:1].[nH:5]1[c:6]([Cl:7])[n:8][c:9]2[c:10]1[c:11](=[O:12])[n:13]([CH3:14])[c:15](=[O:16])[n:17]2[CH3:18]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([Cl:7])[n:8][c:9]2[c:10]1[c:11](=[O:12])[n:13]([CH3:14])[c:15](=[O:16])[n:17]2[CH3:18] | CC#CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O | CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12](-[Cl;D1;H0:13]):[nH;D2;+0:14]:[c:15]:2:[c:16]:1=[O;D1;H0:17]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12](-[Cl;D1;H0:13]):[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;... | null | [] | null | null | 8 | HOUR | 8-Chlorotheophylline (4.9 g) and potassium carbonate (5 g) were dissolved in N,N-dimethylformamide (100 ml), and 1-bromo-2-butyne (2.4 ml) was added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected thro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC#CCBr.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b466f9e290f84d64be09facaa5bd3ad5 | CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | C(C#CC)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)Cl.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)C)=O)C | Cl[c:6]1[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:22]2[c:21]([n:20]1)[n:29]([CH3:30])[c:27](=[O:28])[n:25]([CH3:26])[c:23]2=[O:24].[NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([... | CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]#[C:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]#[C:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 56.9 | [{"value": 56.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Chlorotheophylline (4.9 g) and potassium carbonate (5 g) were dissolved in N,N-dimethylformamide (100 ml), and 1-bromo-2-butyne (2.4 ml) was added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected thro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | null | null | null | CC#CCn1c(Cl)nc2c1c(=O)n(C)c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f81057871ff4374953b46e6470ebbd7 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>>CC#CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)C)=O)C>>C(C#CC)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:15]3[c:14]([n:13]2)[n:22]([CH3:23])[c:20](=[O:21])[n:18]([CH3:19])[c:16]3=[O:17])[CH2:12][CH2:11]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][c:14]2[c:15]1[c:16](=[O:17])[n:18]([CH3:19])[c:20... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | CC#CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C | null | null | FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 84.3 | [{"value": 84.3, "product": "C(C#CC)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-[7-(2-Butynyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (2.5 g) was dissolved in trifluoroacetic acid (15 ml), and the solution was stirred at room temperature for 30 minutes. After removing the solvent by distillation at reduced pressure, the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | FC(C(=O)O)(F)F | null | 0.5 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>FC(C(=O)O)(F)F>CC#CCn1c(N2CCNCC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0e7e5f9437c441f8924ef16ae231e4b | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1>>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1 | C(C)N(CC)CC.ClC(=O)OCC(C)C.C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C(=O)O>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CO | O=[C:20]([CH:19]1[N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22]1)[OH:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:19]([CH2:20][OH... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | C1CNCCN1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4]-[#7:5])-[#7:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C:14]>>[#7:5]-[C:4]-[C:3](-[CH2;D2;+0:1]-[O;D1;H1:2])-[#7:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C:14] | 68.7 | [{"value": 68.7, "product": "C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Triethylamine (6.06 g) and isobutyl chloroformate (7.51 g) were added to a solution of piperazine-1,2,4-tricarboxylic acid 1,4-di-tert-butyl ester (16.52 g) in tetrahydrofuran (200 ml) at −10° C., and the mixture was stirred for 3 hours. The reaction solution was filtered, and treated with 20 ml aqueous solution of sod... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1C[NH]CC[NH]1 | Other | O1CCCC1 | null | 3 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1>O1CCCC1>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-481d891505d2470498fdb98a57d6e16d | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1>>CC(C)(C)OC(=O)N1CCNC(CO)C1 | [OH-].[Na+].C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)CO>>C(C)(C)(C)OC(=O)N1CC(NCC1)CO | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH:12]1[CH2:13][OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH:12]([CH2:13][OH:14])[CH2:15]1 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1 | CC(C)(C)OC(=O)N1CCNC(CO)C1 | null | null | C(C)O | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CNCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1-[C:7]>>[C:7]-[C:6]1-[C:5]-[#7:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 113.9 | [{"value": 113.9, "product": "C(C)(C)(C)OC(=O)N1CC(NCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydroxide (5.42 g) was added to a solution of 2-hydroxymethylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester (10.87 g) in ethanol (300 ml), and the reaction mixture was heated to reflux for 16 hours. The solvent was removed by distillation at reduced pressure, and the residue was dissolved in ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | HO- | C(C)O | null | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(CO)C1>C(C)O>CC(C)(C)OC(=O)N1CCNC(CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2576c0151bb84e62969ea4f8de3c958c | C#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>>C=C=Cn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | [Cl-].[NH4+].C(C)(C)(C)O.CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#C)=O)C)=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C=C=C)=O)C)=O)C | [CH:1]#[C:2][CH2:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]2)[n:19][c:20]2[c:21]1[c:22](=[O:23])[n:24]([CH3:25])[c:26](=[O:27])[n:28]2[CH3:29]>>[CH2:1]=[C:2]=[CH:3][n:4]1[c:5]([N:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[... | C#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | C=C=Cn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | null | null | O.CS(=O)C.C(C)(=O)OCC | Miscellaneous | OtherReaction | 2f13f6ad84546451f3d01481775a52c4098398348b523c935b8104d01b87fd5f | a396e5546fe76b7265b1c53702233ee449ddd085280941b2992883e25d48851e | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | [#7;a:1]:[c:2]:[c:3]1:[#7;a:4](-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[CH;D1;+0:7]):[c:8]:[#7;a:9]:[c:10]:1:[#7;a:11]>>[#7;a:1]:[c:2]:[c:3]1:[#7;a:4](-[CH;D2;+0:5]=[C;H0;D2;+0:6]=[CH2;D1;+0:7]):[c:8]:[#7;a:9]:[c:10]:1:[#7;a:11] | 43.8 | [{"value": 43.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C=C=C)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Tert-butanol (0.1 ml) and potassium tert-butoxide (0.015 g) were added to a solution of 4-[1,3-dimethyl-2,6-dioxo-7-(2-propynyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.402 g) in dimethyl sulfoxide (5 ml), and the reaction mixture was stirred at room temperature for 16 hours. S... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Allene | null | null | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | null | O.CS(=O)C.C(C)(=O)OCC | null | 16 | C#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C>O.CS(=O)C.C(C)(=O)OCC>C=C=Cn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c57168f093724e30ac4695ae5b8c804d | CC#CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C | CN1C(NC(C=2NC=NC12)=O)=O.C([O-])([O-])=O.[K+].[K+].BrCC#CC>>C(C#CC)N1C=NC=2N(C(NC(C12)=O)=O)C | Br[CH2:4][C:3]#[C:2][CH3:1].[nH:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH3:16] | CC#CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[c:15]:1:[#7;a:14]:[c:13]:[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4] | null | [] | null | null | 8 | HOUR | 3-Methylxanthine (1.1 g) was dissolved in N,N-dimethylformamide (15 ml), and potassium carbonate (1.0 g) and 1-bromo-2-butyne (0.64 ml) were added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC#CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>CN(C=O)C.C(C)(=O)OCC>CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4189e519928a47938291124a427688d4 | CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C.O=C1CCC(=O)N1Cl>>CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C | C(C#CC)N1C=NC=2N(C(NC(C12)=O)=O)C.ClN1C(CCC1=O)=O>>C(C#CC)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[cH:6][n:8][c:9]2[c:10]1[c:11](=[O:12])[nH:13][c:14](=[O:15])[n:16]2[CH3:17].O=C1CCC(=O)N1[Cl:7]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([Cl:7])[n:8][c:9]2[c:10]1[c:11](=[O:12])[nH:13][c:14](=[O:15])[n:16]2[CH3:17] | CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C.O=C1CCC(=O)N1Cl | CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | dfc8035b9f4442cdf7ad3396de3c616a20086152342f560e0286a40409232788 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4]1:[#7;a:5](-[C:6]-[C:7]#[C:8]):[cH;D2;+0:9]:[#7;a:10]:[c:11]:1:[#7;a:12]>>[#7;a:2]:[c:3]:[c:4]1:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c;H0;D3;+0:9](-[Cl;H0;D1;+0:1]):[#7;a:10]:[c:11]:1:[#7;a:12] | 73.1 | [{"value": 73.1, "product": "C(C#CC)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3-Methylxanthine (1.1 g) was dissolved in N,N-dimethylformamide (15 ml), and potassium carbonate (1.0 g) and 1-bromo-2-butyne (0.64 ml) were added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2[nH]cnc2n1.C1CCNC1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 3 | CC#CCn1cnc2c1c(=O)[nH]c(=O)n2C.O=C1CCC(=O)N1Cl>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b120fbfc5814f7b8398ed8a595df3b1 | CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | C(C#CC)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)C | Cl[c:6]1[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:22]2[c:21]([n:20]1)[n:28]([CH3:29])[c:26](=[O:27])[nH:25][c:23]2=[O:24].[NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])(... | CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]#[C:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]#[C:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 49.3 | [{"value": 49.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methylxanthine (1.1 g) was dissolved in N,N-dimethylformamide (15 ml), and potassium carbonate (1.0 g) and 1-bromo-2-butyne (0.64 ml) were added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ncc2[nH]cnc2n1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | null | null | null | CC#CCn1c(Cl)nc2c1c(=O)[nH]c(=O)n2C.CC(C)(C)OC(=O)N1CCNCC1>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-114b8ffc9eab403194a1dff7ee465f7f | BrCCOC1CCCCO1.CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCO)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)C.C([O-])([O-])=O.[K+].[K+].BrCCOC1OCCCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCO)=O)C | Br[CH2:26][CH2:27][O:28]C1CCCCO1.[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[c:23](=[O:24])[nH:25][c:29](=[O:30])[n:31]2[CH3:32]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:... | BrCCOC1CCCCO1.CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCO)c(=O)n2C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4282c93c7cb147996e0279746cf436cab34cc0ea5bcd2f4a3e3c08f0606dfd0b | 99bb6d9234ad4c68b21abd97484a68f1ed0a9dfeb0ccd83bf5a372d494646f20 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]#[C:5]-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:4]#[C:5]-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D... | null | [] | null | null | 8 | HOUR | 4-[3-Methyl-7-(2-butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.30 g) and potassium carbonate (0.21 g) were dissolved in N,N-dimethylformamide (10 ml), and 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.23 ml) was added thereto. After stirring at room temperature overnight... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether | Primary alcohol | C1CCOCC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | BrCCOC1CCCCO1.CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCO)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4bd730bec8bb45b088e1ab3e9e0589e1 | O=C(CBr)c1ccccc1>>OC(CBr)c1ccccc1 | BrCC(=O)C1=CC=CC=C1.B.CNC.CO.Cl>>BrCC(O)C1=CC=CC=C1 | [O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[OH:1][CH:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | O=C(CBr)c1ccccc1 | OC(CBr)c1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [Br;D1;H0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[Br;D1;H0:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 60 | HOUR | 2-Bromoacetophenone (1 g) was dissolved in tetrahydrofuran (8 ml), and a solution of borane-dimethylamine (326 mg) in tetrahydrofuran (6 ml) was added thereto at room temperature. After the reaction mixture was stirred at room temperature for 60 hours, methanol (1 ml) and 1 M hydrochloric acid aqueous solution (5 ml) w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | O1CCCC1 | null | 60 | O=C(CBr)c1ccccc1>O1CCCC1>OC(CBr)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2b350801265443084896916d7bc9f99 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CBr>>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC=C(C)C)=O)=O)C.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)CC(=O)O)=O)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][n:6]1[c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[n:21][c:22]2[c:23]1[c:24](=[O:25])[nH:26][c:31](=[O:32])[n:33]2[CH3:34].CC[O:30][C:28]([CH2:27]Br)=[O:29]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][n:6]1[c:7]([N:8]2[CH2:9][CH... | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CBr | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | ad1d146c5db2b34ffa517a98e1bcdbb9faf87e063c8dd5d8f34a5a3425fd43b9 | bb8c9cbffd0728fccf6e94a36c447b744f8891f8faf7c54ceec728809fb06a61 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C.[C:5]=[C:6]-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[#7;a:12](-[C;D1;H3:13]):[c:14](=[O;D1;H0:15]):[nH;D2;+0:16]:[c:17](=[O;D1;H0:18]):[c:19]:1:2>>[C:5]=[C:6]-[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[#7;a:12](-[C;D1;H3:13]):[c:14](=[O;D1;H0:15]):[n;H0;D3;+0:16](-[... | null | [] | null | null | 8 | HOUR | 4-[3-Methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (70 mg) and potassium carbonate (28 mg) were dissolved in N,N-dimethylformamide (1.5 ml), and ethyl bromoacetate (22 μl) was added thereto. After stirring at room temperature overnight, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Carboxylic acid | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C.CCOC(=O)CBr>CN(C=O)C.C(C)(=O)OCC>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64fa72b927814a699b52cedc35fe91ee | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C>>CC(C)=CCn1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)CC(=O)O)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.CN1C(N(C(C=2N(C(=NC12)N1CCNCC1)CC=C(C)C)=O)CC(=O)O)=O | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][N:8]([c:7]2[n:6]([CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[c:16]3[c:15]([n:14]2)[n:26]([CH3:27])[c:24](=[O:25])[n:19]([CH2:20][C:21](=[O:22])[OH:23])[c:17]3=[O:18])[CH2:13][CH2:12]1>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][n:6]1[c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[n:14][c:15]... | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | CC(C)=CCn1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | 30 | MINUTE | 4-[3-Methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (70 mg) and potassium carbonate (28 mg) were dissolved in N,N-dimethylformamide (1.5 ml), and ethyl bromoacetate (22 μl) was added thereto. After stirring at room temperature overnight, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | null | null | 0.5 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C>>CC(C)=CCn1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-480476da2ef24e60b6fbd0355d35cc33 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>>Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O | ClC1=NC=2N(C(N(C)C(C2N1)=O)=O)C.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)C)=O)C | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.Cl[c:7]1[nH:6][c:5]2[c:3](=[O:4])[n:2]([CH3:1])[c:25](=[O:26])[n:23]([CH3:24])[c:22]2[n:21]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[nH:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3... | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O | Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C;D1;H3:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:1.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C;D1;H3:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[#7;a:10]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]3-[C:15]-[C:16]-[#7:11]-[C:12]-[C:13]-3):[#7;a:2]:[c:3]:1:2 | 61.4 | [{"value": 61.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 8 | HOUR | 8-Chlorotheophylline (3.5 g) and piperazine-1-carboxylic acid tert-butyl ester (11.69 g) were mixed, and stirred at 110° C. overnight. Then, the reaction mixture was diluted with ethyl acetate and water, insoluble white solid was collected by filtration, and washed with ethyl acetate to give 3.65 g of the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1C[NH]CC[NH]1 | c1ncc2[nH]cnc2n1.C1C[NH]CC[NH]1 | HCl | O.C(C)(=O)OCC | 110 | 8 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2[nH]c(Cl)nc2n(C)c1=O>O.C(C)(=O)OCC>Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93a2667b2efd416687c537c2fcad7768 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21>>Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1 | ClC1=NC=2N(C(NC(C2N1)=O)=O)C.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][c:11]([Cl:12])[nH:13]2>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][c:11]([Cl:12])[n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21 | Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13](-[Cl;D1;H0:14]):[#7;a:15]:[c:16]:1:2>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[c:16]:1:[#7;a:15]:[c:13](-[Cl;D1;H0:14]):[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4... | null | [] | null | null | 13 | HOUR | 8-Chloro-3-methyl-3,7-dihydropurine-2,6-dione (200 mg) and potassium carbonate (152 mg) were suspended in N,N-dimethylformamide (10 ml), and benzyl bromide was added dropwise thereto while cooling on ice. The reaction mixture was left standing till reaching room temperature, and was stirred at room temperature for 13 h... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | O.CN(C=O)C.C(C)(=O)OCC | null | 13 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]c(Cl)nc21>O.CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bae984a2d7ad483fb5f6c32628af5994 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1>>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1 | C(C1=CC=CC=C1)N1C(=NC=2N(C(NC(C12)=O)=O)C)Cl.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC1=CC=CC=C1)=O)=O)C | [NH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1.Cl[c:11]1[n:10][c:9]2[n:2]([CH3:1])[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[n:25]1[CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][c:11]([N:12]1[CH2:... | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1 | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a7281e2244df3601ecd9ce5717fbabd29c2b0a900306db46e15732281e06263f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2Cc2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:4]:[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[#7;a:8](-[C:9]):[c:5]:1:[c:6]:[#7;a:7] | 96.5 | [{"value": 96.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC1=CC=CC=C1)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Benzyl-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione (130 mg) and 1-piperazine carboxylic acid tert-butyl ester (250 mg) were stirred at 150° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, and the resulting suspension was filtered to give white solid. This solid was purified by silica gel column ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2Cc1ccccc1>C(C)(=O)OCC>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c160725f5b994922ab6667caaefb209c | CCOC(=O)CBr.Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1>>CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC1=CC=CC=C1)=O)=O)C.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC1=CC=CC=C1)=O)CC(=O)OCC)=O)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[c:8](=[O:9])[c:10]2[c:11]([n:12][c:13]([N:14]3[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[n:27]2[CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[n:35]([CH3:36])[c:37]1=[O:38]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2... | CCOC(=O)CBr.Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1 | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])... | null | [] | null | null | 8 | HOUR | 4-[7-(Benzyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (182 mg) was dissolved in N,N-dimethylformamide (2 ml), and potassium carbonate (90 mg) and ethyl bromoacetate (0.06 ml) were added thereto. The reaction solution was stirred at room temperature overnight, di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CCOC(=O)CBr.Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4374c8aae1004adb81c7f8b9ff4f53f8 | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O>>CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC1=CC=CC=C1)=O)CC(=O)OCC)=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)CC(=O)OCC)=O)C | c1ccc(C[n:11]2[c:10]3[c:8](=[O:9])[n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[n:28]([CH3:29])[c:27]3[n:26][c:12]2[N:13]2[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[c:10]2[nH:11][c:12]([... | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O | CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O | null | [OH-].[Pd+2].[OH-] | C(C)(=O)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13](=[O;D1;H0:14]):[c:15]:2:[n;H0;D3;+0:16]:1-C-c1:c:c:c:c:c:1>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13](=[O;D1;H0:14]):[c:15]:2:[nH;D2;+0:... | null | [] | null | null | 8 | HOUR | 4-[7-Benzyl-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester was dissolved in acetic acid, and palladium hydroxide (ca. 10 mg) was added thereto. The reaction mixture was stirred at room temperature under hydrogen atmosphere overnight, filtered, ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1C[NH]CC[NH]1 | Other | [OH-].[Pd+2].[OH-].C(C)(=O)O | null | 8 | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2Cc2ccccc2)n(C)c1=O>[OH-].[Pd+2].[OH-].C(C)(=O)O>CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-afa96f505db54a0193b7dfd6f420b2c1 | CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.COc1ccccc1B(O)O>>CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)CC(=O)OCC)=O)C.COC1=C(C=CC=C1)B(O)O.N1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)OCC)=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[c:10]2[c:11]([n:12][c:13]([N:14]3[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[nH:27]2)[n:36]([CH3:37])[c:38]1=[O:39].OB(O)[c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[O:34][CH3:35]>>[CH3:1][CH2:2][O:3][C:4](=[O... | CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.COc1ccccc1B(O)O | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 193a52be698a8cc7c00a0e51f250e81e1eef3fc7f6e6eee9787e052516f6fde7 | e0368246531386f86cd0aa9da1423eb47f529b782fb229563cefe1166d6ba4f5 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]-[c:8]1:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13]:[#7;a:14](-[C:15]-[C:16](-[#8:17])=[O;D1;H0:18]):[c:19](=[O;D1;H0:20]):[c:21]:2:[nH;D2;+0:22]:1>>[#7:7]-[c:8]1:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13]:[#7;a:14](-[C:15]-[C:16](-[#8:17])=[O;D... | null | [] | null | null | 3 | DAY | 4-[1-(Ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester, 2-methoxyphenyl boronic acid (60 mg), and copper (II) acetate (200 mg) were dissolved in anhydrous tetrahydrofuran (5 ml), and pyridine (0.2 ml) was added thereto. The reaction mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O1CCCC1 | null | 72 | CCOC(=O)Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.COc1ccccc1B(O)O>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O1CCCC1>CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-518e1b1ab51c4b65998c1f7a79d814ce | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O>>CCOC(=O)Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2OC)n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)OCC)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.C(C)OC(CN1C(N(C=2N=C(N(C2C1=O)C1=C(C=CC=C1)OC)N1CCNCC1)C)=O)=O | CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][N:14]([c:13]2[n:12][c:11]3[c:10]([c:8](=[O:9])[n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:31](=[O:32])[n:29]3[CH3:30])[n:20]2-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[O:27][CH3:28])[CH2:19][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[c:10]2[c:11]([n:... | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O | CCOC(=O)Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2OC)n(C)c1=O | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 30 | MINUTE | 4-[7-(2-Methoxyphenyl)-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (10 mg) was dissolved in trifluoroacetic acid (0.5 ml), and the reaction mixture was stirred at room temperature for 30 minutes. After the solvent was removed, the residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ncc2nc[nH]c2n1.C1C[NH]CCN1.c1ccccc1 | HO- | null | null | 0.5 | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O>>CCOC(=O)Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2OC)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1cf50f5eddd44248e3f17ee0a83697f | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O>>COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)OCC)=O)C.[OH-].[Na+].Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)O)=O)C | CC[O:33][C:31]([CH2:30][n:29]1[c:27](=[O:28])[c:26]2[n:9](-[c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[n:24][c:25]2[n:36]([CH3:37])[c:34]1=[O:35])=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8... | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O | COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 35.2 | [{"value": 35.2, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 4-[7-(2-Methoxyphenyl)-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (9 mg) was dissolved in ethanol (1 ml), and 5 N sodium hydroxide aqueous solution (0.1 ml) was added thereto. The reaction mixture was left standing at room temperature for 5... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | Other | C(C)O | null | 5 | CCOC(=O)Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2OC)n(C)c1=O>C(C)O>COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ceea3281bb1491ebbae20028e5ddf5e | COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C>>COc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)OC)=O)CC(=O)O)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.COC1=C(C=CC=C1)N1C(=NC=2N(C(N(C(C12)=O)CC(=O)O)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([c:10]2[n:9](-[c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[c:19]3[c:18]([n:17]2)[n:29]([CH3:30])[c:27](=[O:28])[n:22]([CH2:23][C:24](=[O:25])[OH:26])[c:20]3=[O:21])[CH2:16][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2:12][CH2:13][... | COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | COc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 30 | MINUTE | 4-[7-(2-Methoxyphenyl)-1-(carboxymethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (3 mg) was dissolved in trifluoroacetic acid (0.5 ml), and the reaction mixture was stirred at room temperature for 30 minutes. After the solvent was removed, the residue was purifi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | null | null | 0.5 | COc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C>>COc1ccccc1-n1c(N2CCNCC2)nc2c1c(=O)n(CC(=O)O)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de5ab057cc874dc8a359fec67745cd09 | Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.O=Cc1ccccc1B(O)O>>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)C)=O)C.C(=O)C1=C(C=CC=C1)B(O)O.N1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)C)=O)C | [CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]3)[nH:22]2)[n:31]([CH3:32])[c:33]1=[O:34].OB(O)[c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[CH:29]=[O:30]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][C... | Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.O=Cc1ccccc1B(O)O | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 193a52be698a8cc7c00a0e51f250e81e1eef3fc7f6e6eee9787e052516f6fde7 | e0368246531386f86cd0aa9da1423eb47f529b782fb229563cefe1166d6ba4f5 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].[#7:8]-[c:9]1:[#7;a:10]:[c:11]2:[#7;a:12](-[C;D1;H3:13]):[c:14]:[#7;a:15](-[C;D1;H3:16]):[c:17](=[O;D1;H0:18]):[c:19]:2:[nH;D2;+0:20]:1>>[#7:8]-[c:9]1:[#7;a:10]:[c:11]2:[#7;a:12](-[C;D1;H3:13]):[c:14]:[#7;a:15](-[C;D1;H3:16]):[c:17](=[O;D1;H0:18]):[c:... | 17.6 | [{"value": 17.6, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | 4-(1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (226 mg), 2-formylphenyl boronic acid (200 mg), and copper (II) acetate (200 mg) were suspended in anhydrous tetrahydrofuran (5 ml), and pyridine (0.2 ml) was added thereto. The reaction mixture was stirred at room ... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O1CCCC1 | null | 120 | Cn1c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc2n(C)c1=O.O=Cc1ccccc1B(O)O>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].O1CCCC1>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-905384ce403144c98d18bded1622e2ea | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O.NO>>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=NO)n(C)c1=O | C(C)(=O)[O-].[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)C)=O)C.Cl.NO>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=NO)=O)C)=O)C | O=[CH:29][c:28]1[c:23](-[n:22]2[c:5]3[c:3](=[O:4])[n:2]([CH3:1])[c:34](=[O:35])[n:32]([CH3:33])[c:6]3[n:7][c:8]2[N:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2)[cH:24][cH:25][cH:26][cH:27]1.[NH2:30][OH:31]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH... | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O.NO | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=NO)n(C)c1=O | null | null | O.C(C)(=O)OCC.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H1:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 0.5 | HOUR | 4-[7-(2-Formylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (13 mg) and hydroxylamine hydrochloride (10 mg) were dissolved in ethanol (1 ml) and water (0.2 ml), and potassium acetate (ca. 10 mg) was added thereto. The reaction solution was stirred for 0.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O.C(C)(=O)OCC.C(C)O | null | 0.5 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O.NO>O.C(C)(=O)OCC.C(C)O>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=NO)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87bf5a0a465d4a4db4478eb252cf06f8 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O>>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2CO)n(C)c1=O | [BH4-].[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)C)=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)CO)=O)C)=O)C | [CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]3)[n:22]2-[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[CH:29]=[O:30])[n:31]([CH3:32])[c:33]1=[O:34]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11]... | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2CO)n(C)c1=O | null | null | O1CCCC1.C(C)(=O)OCC.C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 103.3 | [{"value": 103.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)CO)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-[7-(2-Formylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (27 mg) was dissolved in anhydrous tetrahydrofuran (0.5 ml) and ethanol (0.5 ml), and sodium borohydride (20 mg) was added thereto. The reaction solution was stirred at room temperature for 1 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | null | O1CCCC1.C(C)(=O)OCC.C(C)O | null | 1 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O>O1CCCC1.C(C)(=O)OCC.C(C)O>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2CO)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ada8ac12677340b39fd183138d9946c7 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | CC(C)([O-])C.[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=O)=O)C)=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)C)=O)C | O=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]2)[n:24][c:25]2[c:26]1[c:27](=[O:28])[n:29]([CH3:30])[c:31](=[O:32])[n:33]2[CH3:34]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:10]([N:11]2[CH2... | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O1CCCC1.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 200.8 | [{"value": 200.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Potassium tert-butoxide (9 mg) was dissolved in tetrahydrofuran (1 ml), and methyl triphenyl phosphonium bromide (31 mg) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes, and a solution of 4-[7-(2-formylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-ca... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1.C(C)(=O)OCC | null | 0.5 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2C=O)n(C)c1=O>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1.C(C)(=O)OCC>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(C)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a5fdccb69a534845ac96f83401c57e39 | Cn1c(=O)c2[nH]cnc2n(C)c1=O.OB(O)c1ccccc1Cl>>Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O | N1(C)C(=O)N(C)C=2N=CNC2C1=O.ClC1=C(C=CC=C1)B(O)O.N1=CC=CC=C1>>ClC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C | [CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][nH:9]2)[n:17]([CH3:18])[c:19]1=[O:20].OB(O)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][n:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[n:17]([CH3:18])[c:19]1=[O:20] | Cn1c(=O)c2[nH]cnc2n(C)c1=O.OB(O)c1ccccc1Cl | Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 193a52be698a8cc7c00a0e51f250e81e1eef3fc7f6e6eee9787e052516f6fde7 | e0368246531386f86cd0aa9da1423eb47f529b782fb229563cefe1166d6ba4f5 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2)[nH]1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C;D1;H3:7]-[#7;a:8]1:[c:9]:[#7;a:10](-[C;D1;H3:11]):[c:12](=[O;D1;H0:13]):[c:14]2:[nH;D2;+0:15]:[c:16]:[#7;a:17]:[c:18]:1:2>>[C;D1;H3:7]-[#7;a:8]1:[c:9]:[#7;a:10](-[C;D1;H3:11]):[c:12](=[O;D1;H0:13]):[c:14]2:[c:18]:1:[#7;a:17]:[c:16]:[n;H0;D3;+0:15]:2-[c;... | 17.9 | [{"value": 17.9, "product": "ClC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Theophylline (510 mg), 2-chlorophenyl boronic acid (1 g), and copper (II) acetate (220 mg) were suspended in N,N-dimethylformamide (10 ml), and pyridine (1 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 30% aqueous ammonia. The organic ... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C=O)C.C(C)(=O)OCC | null | 8 | Cn1c(=O)c2[nH]cnc2n(C)c1=O.OB(O)c1ccccc1Cl>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5998921bf56e49cb9138c95f91cbe32a | Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O.O=C1CCC(=O)N1Cl>>Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O | ClC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)C.ClN1C(CCC1=O)=O>>ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C | [CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][n:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[n:18]([CH3:19])[c:20]1=[O:21].O=C1CCC(=O)N1[Cl:9]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([Cl:9])[n:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[n:18]([CH3:19])[c:20]1=[O:21] | Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O.O=C1CCC(=O)N1Cl | Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | 14c81eccfe7222df9f154a6d36de877a8f4fe32e30972af529ae83dcf968a138 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2)[nH]1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]1:[#7;a:4]:[cH;D2;+0:5]:[#7;a:6](-[c:7]):[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:2]:[c:3]1:[#7;a:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[#7;a:6](-[c:7]):[c:8]:1:[c:9]:[#7;a:10] | 97.8 | [{"value": 97.8, "product": "ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7-(2-Chlorophenyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione (138 mg) and N-chlorosuccinimide (78 mg) were suspended in N,N-dimethylformamide (1 ml). The reaction mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium s... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2nc[nH]c2n1.C1CCNC1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | Cn1c(=O)c2c(ncn2-c2ccccc2Cl)n(C)c1=O.O=C1CCC(=O)N1Cl>CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1136e65f66bf452d8e71c88c0c626771 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O>>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O | ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Cl[c:8]1[n:7][c:6]2[c:5]([c:3](=[O:4])[n:2]([CH3:1])[c:32](=[O:33])[n:30]2[CH3:31])[n:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[Cl:29]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11][N:... | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a7281e2244df3601ecd9ce5717fbabd29c2b0a900306db46e15732281e06263f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[c:9]):[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 68.9 | [{"value": 68.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 4 | HOUR | 8-Chloro-7-(2-chlorophenyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione (142 mg) and piperazine-1-carboxylic acid tert-butyl ester (500 mg) were mixed, and the reaction mixture was stirred at 150° C. for 4 hours, diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)(=O)OCC | 150 | 4 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O>C(C)(=O)OCC>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4c8e39431ef46498ae1c005321f4aff | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O>>Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(C)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C>>ClC1=C(C=CC=C1)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([c:8]2[n:7][c:6]3[c:5]([c:3](=[O:4])[n:2]([CH3:1])[c:25](=[O:26])[n:23]3[CH3:24])[n:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[CH2:14][CH2:13]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15]2-[c:16]2[cH:17][... | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O | Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(C)c1=O | null | null | FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 135.4 | [{"value": 135.4, "product": "ClC1=C(C=CC=C1)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-[7-(2-Chlorophenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (102 mg) was dissolved in trifluoroacetic acid (5 ml), and the solution was stirred at room temperature for 30 minutes. After the solvent was removed, the residue was purified by column chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ncc2nc[nH]c2n1.C1C[NH]CCN1.c1ccccc1 | HO- | FC(C(=O)O)(F)F | null | 0.5 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C)c1=O>FC(C(=O)O)(F)F>Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58313497266c441c9a701507bdd5b267 | COC(=O)C1CC(OS(C)(=O)=O)CN1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO | Cl.[BH4-].[Li+].COC(=O)C1N(CC(C1)OS(=O)(=O)C)C(=O)OC(C)(C)C.[BH4-].[Li+]>>C(C)(C)(C)OC(=O)N1C(CC(C1)OS(=O)(=O)C)CO | CO[C:18]([CH:17]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]([O:11][S:12]([CH3:13])(=[O:14])=[O:15])[CH2:16]1)=[O:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][S:12]([CH3:13])(=[O:14])=[O:15])[CH2:16][CH:17]1[CH2:18][OH:19] | COC(=O)C1CC(OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13] | 95.2 | [{"value": 95.2, "product": "C(C)(C)(C)OC(=O)N1C(CC(C1)OS(=O)(=O)C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-(Methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.972 g) was dissolved in tetrahydrofuran (40 ml), and lithium borohydride (300 mg) was added thereto. The reaction mixture was stirred at room temperature overnight, additional lithium borohydride (1000 mg) was added, and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1 | Other | O1CCCC1 | null | 8 | COC(=O)C1CC(OS(C)(=O)=O)CN1C(=O)OC(C)(C)C>O1CCCC1>CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-098a1780650b479d922e2c00fd2fd91e | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1COS(C)(=O)=O | C(C)(C)(C)OC(=O)N1C(CC(C1)OS(=O)(=O)C)CO.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N1C(CC(C1)OS(=O)(=O)C)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][S:12]([CH3:13])(=[O:14])=[O:15])[CH2:16][CH:17]1[CH2:18][OH:19].Cl[S:20]([CH3:21])(=[O:22])=[O:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][S:12]([CH3:13])(=[O:14])=[O:15])[CH2:16][CH:17]1[CH2:18][O:19][S:20]... | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1COS(C)(=O)=O | null | null | N1=CC=CC=C1.C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#7:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 8 | HOUR | 2-(Hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester (1.715 g) was dissolved in pyridine (20 ml), and methanesulfonylchloride (0.6 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | N1=CC=CC=C1.C(C)(=O)OCC | null | 8 | CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1CO.CS(=O)(=O)Cl>N1=CC=CC=C1.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CC(OS(C)(=O)=O)CC1COS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f9c3b3406294c98a9964679f62bb457 | Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F>>Cn1c(=O)c2c(nc(N3CC4CC3CN4)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F | ClC1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.ClC1=C(C=CC=C1)N1C(=NC=2N(C(N(C(C12)=O)C)=O)C)N1C2CNC(C1)C2 | Cl[c:8]1[n:7][c:6]2[c:5]([c:3](=[O:4])[n:2]([CH3:1])[c:26](=[O:27])[n:24]2[CH3:25])[n:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Cl:23].[C:10]([C:14](=[O:28])[OH:30])([F:32])([F:33])[F:34]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH:11]4[CH2:12][CH:13]3[CH2:14][NH:15]4)[n:16]2-[c:17]2[cH:18... | Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F | Cn1c(=O)c2c(nc(N3CC4CC3CN4)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F | null | null | null | Acylation | OtherReaction | dd078d496b9b4fb86302aff7d040dae5217a2b412f12f4e939a10daa1d2313a7 | cdffa2f425372a39a05530afe78b4ebe6db8a2f3f2ba1b01eb62c2edb35cde1d | O=c1[nH]c(=O)c2c(nc(N3CC4CC3CN4)n2-c2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9].[F;H0;D1;+0:10]-[C;H0;D4;+0:11](-[F;H0;D1;+0:12])(-[F;H0;D1;+0:13])-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[OH;D1;+0:16]>>[#7;a:4]:[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[#7:17]2-[CH2;D2;+0:11]-[C:18]3-[#7:19]-[CH2;D2;+0:14]-[C:20]-2-[C:21]-3):[#7... | null | [] | 150 | CELSIUS | 3 | HOUR | 2,5-(Diaza-bicyclo[2.2.1]heptane)-2-carboxylic acid tert-butyl ester (50 mg) and 8-chloro-7-(2-chlorophenyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione (10 mg) were mixed, and the mixture was stirred at 150° C. for 3 hours. The residue was dissolved in trifluoroacetic acid, and the solution was concentrated. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Carboxylic acid | Trifluoro group.Carboxylic acid.Secondary amine.Tertiary amine | c1ncc2nc[nH]c2n1 | C1[NH]C2CNC1C2.c1ncc2nc[nH]c2n1 | C1[NH]C2CNC1C2.c1ncc2nc[nH]c2n1.c1ccccc1 | null | null | 150 | 3 | Cn1c(=O)c2c(nc(Cl)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F>>Cn1c(=O)c2c(nc(N3CC4CC3CN4)n2-c2ccccc2Cl)n(C)c1=O.O=C(O)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af1959f7521043bca05950b1fe807b59 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CN1C(NC(C=2NC=NC12)=O)=O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][cH:11][nH:12]2>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][cH:11][n:12]2[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[c:15]:1:[#7;a:14]:[c:13]:[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | 3-Methylxanthine (2.882 g) was suspended in N,N-dimethylformamide (40 ml), and potassium carbonate (3 g) and benzyl bromide (2.5 ml) was added thereto. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. The deposited crystals were collected... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | BrCc1ccccc1.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ca37fb865514730bd2ab9e8ca778ed3 | CC(C)(C)C(=O)OCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1 | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C.C([O-])([O-])=O.[K+].[K+].C(C(C)(C)C)(=O)OCCl>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COC(C(C)(C)C)=O)=O)C | Cl[CH2:6][O:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:14](=[O:15])[c:16]2[c:17]1[n:18][cH:19][n:20]2[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][O:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[c:17]1[n:... | CC(C)(C)C(=O)OCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:15]1:[c:16](=[O;D1;H0:17]):[c:18]2:[#7;a:7](-[C:6]):[c:8]:[#7;a:9]:[c:10]:2:[... | null | [] | 40 | CELSIUS | 8 | HOUR | 7-Benzyl-3-methyl-3,7-dihydropurine-2,6-dione (3.18 g) was suspended in N,N-dimethylformamide (40 ml), and potassium carbonate (2.6 g) and chloromethyl pivalate (2.15 ml) were added thereto. The reaction solution was stirred at 40° C. overnight, then diluted with ethyl acetate, and washed with 1 N hydrochloric acid. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | 40 | 8 | CC(C)(C)C(=O)OCCl.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ccd82a36e79434a81b3766ff31c1625 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1>>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]cnc21 | C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COC(C(C)(C)C)=O)=O)C>>CN1C(N(C(C=2NC=NC12)=O)COC(C(C)(C)C)=O)=O | c1ccc(C[n:17]2[c:16]3[c:14](=[O:15])[n:5]([CH2:6][O:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[c:3](=[O:4])[n:2]([CH3:1])[c:20]3[n:19][cH:18]2)cc1>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][O:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[nH:17][cH:18][n:19][c:20]12 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]cnc21 | null | [Pd] | C(C)(=O)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[n;H0;D3;+0:9](-C-c3:c:c:c:c:c:3):[c:10]:2:[c:11]:1=[O;D1;H0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:2:[c:11]:1=[O;D1;H0:12] | 92.4 | [{"value": 92.4, "product": "CN1C(N(C(C=2NC=NC12)=O)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2,2-Dimethylpropionic acid 7-benzyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydropurin-1-ylmethyl ester (4.26 g) was dissolved in acetic acid (100 ml), and 10% palladium on carbon (1.5 g) was added thereto. The reaction mixture was stirred under hydrogen atmosphere at room temperature overnight, filtered through Celite, and th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | [Pd].C(C)(=O)O | null | 8 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2Cc1ccccc1>[Pd].C(C)(=O)O>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]cnc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-545a3981570c46229004ae735ad19ac8 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2-c1ccccc1Cl>>Cn1c(=O)[nH]c(=O)c2c1ncn2-c1ccccc1Cl | [H-].[Na+].ClC1=C(C=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COC(C(C)(C)C)=O)=O)C>>ClC1=C(C=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C | CC(C)(C)C(=O)OC[n:5]1[c:3](=[O:4])[n:2]([CH3:1])[c:9]2[c:8]([c:6]1=[O:7])[n:12](-[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[cH:11][n:10]2>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][cH:11][n:12]2-[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19] | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2-c1ccccc1Cl | Cn1c(=O)[nH]c(=O)c2c1ncn2-c1ccccc1Cl | null | null | O1CCCC1.CO.C(C)(=O)OCC | Reduction | OtherReaction | 15f0619d47e85f67d3db05c38f15a5e9a65c9aacaa3d9463ca5ccdfd111c7722 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(ncn2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c:11]:2:[c:12]:1=[O;D1;H0:13]>>[C;D1;H3:5]-[#7;a:4]1:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:12](=[O;D1;H0:13]):[c:11]2:[#7;a:9](-[c:10]):[c:8]:[#7;a:7]:[c:6]:1:2 | 70.6 | [{"value": 70.6, "product": "ClC1=C(C=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2,2-Dimethyl-propionic acid 7-(2-chlorophenyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydropurin-1-ylmethyl ester (144 mg) was dissolved in methanol (2 ml) and tetrahydrofuran (1 ml), and sodium hydride (20 mg) was added thereto. The reaction solution was stirred at room temperature overnight, diluted with ethyl acetate, and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HO- | O1CCCC1.CO.C(C)(=O)OCC | null | 8 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1ncn2-c1ccccc1Cl>O1CCCC1.CO.C(C)(=O)OCC>Cn1c(=O)[nH]c(=O)c2c1ncn2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-427692e7b0994aac9c5bce9e1eba85db | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2-c1ccccc1Cl>>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | ClC1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)C.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)C | [NH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1.Cl[c:11]1[n:10][c:9]2[n:2]([CH3:1])[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[n:25]1-[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32]>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][c:11]([N:12]1[CH2:1... | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2-c1ccccc1Cl | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a7281e2244df3601ecd9ce5717fbabd29c2b0a900306db46e15732281e06263f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:4]:[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[#7;a:8](-[c:9]):[c:5]:1:[c:6]:[#7;a:7] | 51.2 | [{"value": 51.2, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 4 | HOUR | 8-Chloro-7-(2-chlorophenyl)-3-methyl-3,7-dihydropurine-2,6-dione (58 mg) and 1-(tert-butoxycarbonyl)piperazine (150 mg) were mixed. The reaction solution was stirred at 150° C. for 4 hours, then diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)(=O)OCC | 150 | 4 | CC(C)(C)OC(=O)N1CCNCC1.Cn1c(=O)[nH]c(=O)c2c1nc(Cl)n2-c1ccccc1Cl>C(C)(=O)OCC>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75df780a0b9744e38a7dfb977aa4d112 | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.ClC1=C(C=CC=C1)N1C(=NC=2N(C(NC(C12)=O)=O)C)N1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][N:12]([c:11]2[n:10][c:9]3[n:2]([CH3:1])[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]3[n:18]2-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[Cl:25])[CH2:17][CH2:16]1>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[c:8]2[c:9]1[n:10][c:11]([N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)[n:18]2-[c... | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 4-[7-(2-Chlorophenyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (8 mg) was dissolved in trifluoroacetic acid, and the solution was concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 3.86 mg of the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ncc2nc[nH]c2n1.C1C[NH]CCN1.c1ccccc1 | HO- | null | null | null | Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>Cn1c(=O)[nH]c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8edc079a9cfc4fa4baaa2531b276fd8e | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1>>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc21 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC1=CC=CC=C1)=O)COC(C(C)(C)C)=O)=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)COC(C(C)(C)C)=O)=O)C | c1ccc(C[n:17]2[c:16]3[c:14](=[O:15])[n:5]([CH2:6][O:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[c:3](=[O:4])[n:2]([CH3:1])[c:33]3[n:32][c:18]2[N:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)cc1>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][O:7][C:8](=[O:9])[C:10... | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc21 | null | [Pd] | C(C)(=O)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]):[c:10](=[O;D1;H0:11]):[c:12]:2:[n;H0;D3;+0:13]:1-C-c1:c:c:c:c:c:1>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]2:[#7;a:5](-[C;D1;H3:6]):[c:7]:[#7;a:8](-[C:9]):[c:10](=[O;D1;H0:11]):[c:12]:2:[nH;D2;+0:13]:1 | 101.3 | [{"value": 101.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1)=O)COC(C(C)(C)C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[7-Benzyl-1-(2,2-dimethylpropionyloxymethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (2.227 g) was dissolved in acetic acid (100 ml), and 10% palladium on carbon (1 g) was added thereto. The reaction mixture was stirred under hydrogen atmosphere at room temper... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1C[NH]CC[NH]1 | Other | [Pd].C(C)(=O)O | null | 8 | Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2Cc1ccccc1>[Pd].C(C)(=O)O>Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2[nH]c(N3CCN(C(=O)OC(C)(C)C)CC3)nc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6638aa8a8c584c4eb7e91dcb0fd47e00 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2C>>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)C=C)=O)COC(C(C)(C)C)=O)=O)C.[H-].[Na+].Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)C=C)=O)=O)C | CC(C)(C)C(=O)OC[n:29]1[c:27](=[O:28])[c:26]2[n:9](-[c:8]3[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]3)[c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[n:24][c:25]2[n:32]([CH3:33])[c:30]1=[O:31]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[n:9]1[c:... | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2C | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C | null | null | CO | Reduction | OtherReaction | df8a3c8b7aa7d10b48c9fb6d61e80538577be49615529cea0e9d9fc23715d092 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]2:[#7;a:5](-[c:6]):[c:7]:[#7;a:8]:[c:9]:2:[#7;a:10](-[C;D1;H3:11]):[c:12]:1=[O;D1;H0:13]>>[C;D1;H3:11]-[#7;a:10]1:[c:9]2:[#7;a:8]:[c:7]:[#7;a:5](-[c:6]):[c:4]:2:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:12]:1=[O;D1;H0:13] | 72.3 | [{"value": 72.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)C=C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-vinylphenyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (187 mg) was dissolved in methanol (3 ml), and sodium hydride (14 mg) was added thereto. The reaction solution was stirred at room temperature overnight, then neutral... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | CO | null | 8 | C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2C>CO>C=Cc1ccccc1-n1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9349fb20892142b98b4f4d5634f3a1bb | BrCc1ccccc1.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>>Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1 | CO.C(C1=CC=CC=C1)Br.[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(=O)NC(N)=NC12.Cl>>Cl.NC=1NC(C=2N(C=NC2N1)CC1=CC=CC=C1)=O | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.OC[C@H]1O[C@@H]([n:6]2[c:5]3[n:4][c:3]([NH2:2])[nH:19][c:17](=[O:18])[c:16]3[n:8][cH:7]2)[C@H](O)[C@@H]1O>>[NH2:2][c:3]1[n:4][c:5]2[n:6][cH:7][n:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]2[c:17](=[O:18])[nH:19]1 | BrCc1ccccc1.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 9c0b65b3b36e91361057e72b387788b1e8f2aee57ec4e51722f981326e666e78 | 7e189fd7804363b4ff1bb6a3fdde36fc1841a086a68dd39810ea376b719596d5 | O=c1[nH]cnc2ncn(Cc3ccccc3)c12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O-C-[C@@H]1-O-[C@@H](-[n;H0;D3;+0:5]2:[c:6]:[n;H0;D2;+0:7]:[c:8]3:[c:9](=[O;D1;H0:10]):[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:3:2)-[C@H](-O)-[C@H]-1-O>>[O;D1;H0:10]=[c:9]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[n;H0;D2;+0:5]:[c:6]:[n;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8]:1:2 | null | [] | null | null | 4 | HOUR | Benzyl bromide (100 ml) was added dropwise to a suspension of guanosine (100 g) in dimethyl sulfoxide (500 ml) at room temperature, and the resulting reaction mixture was stirred at room temperature for 4 hours. Then, concentrated hydrochloric acid (250 ml) was added thereto. The reaction mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol | null | C1CCOC1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | CS(=O)C | null | 4 | BrCc1ccccc1.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>CS(=O)C>Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed9edb7aaaa148d6b71ad67af5327a84 | Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1>>O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl.NC=1NC(C=2N(C=NC2N1)CC1=CC=CC=C1)=O.N(=O)[O-].[Na+]>>C(C1=CC=CC=C1)N1C=NC=2NC(NC(C12)=O)=O | N[c:2]1[nH:3][c:4](=[O:5])[c:6]2[c:7]([n:8][cH:9][n:10]2[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[c:6]2[c:7]([n:8][cH:9][n:10]2[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[nH:18]1 | Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1 | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | null | null | O.C(C)(=O)O | Functional Group Interconversion | OtherReaction | 88ad41eaab7ae0c57f8310f86ca5aeedc36ef8ec915a6178d78dfbcf9cea7d9e | ca5105ff0b33557e585dc54e7cfdd7fa7df4e7f9c3edc13b706f4674b75a100e | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5](-[C:6]):[c:7]:[#7;a:8]:[c:9]:2:[n;H0;D2;+0:10]:1>>[C:6]-[#7;a:5]1:[c:7]:[#7;a:8]:[c:9]2:[nH;D2;+0:10]:[c;H0;D3;+0:1](=[O;D1;H0:11]):[#7;a:2]:[c:3]:[c:4]:1:2 | 38 | [{"value": 38.0, "product": "C(C1=CC=CC=C1)N1C=NC=2NC(NC(C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 10 | MINUTE | A white suspension of 2-amino-7-benzyl-1,7-dihydropurin-6-one hydrochloride (12.88 g) in acetic acid (320 ml) and water (32 ml) was stirred at 110° C. for 10 minutes, and then at 50° C. for 10 minutes. Aqueous solution (32 ml) of sodium nitrite (12.88 g) was slowly added dropwise at 50° C. thereto. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | null | O.C(C)(=O)O | 110 | 0.166667 | Nc1nc2ncn(Cc3ccccc3)c2c(=O)[nH]1>O.C(C)(=O)O>O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b65da21e126f4f65b15f36373117b212 | CC(C)(C)C(=O)OCCl.CN(C)C=O.O=C([O-])[O-].O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>>CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O | C(C1=CC=CC=C1)N1C=NC=2NC(NC(C12)=O)=O.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].C(C(C)(C)C)(=O)OCCl>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | Cl[CH2:8][O:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:32])=[O:6].O=[CH:25]N([CH3:4])[CH3:30].[O-][C:27]([O-:26])=[O:28].[nH:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:33]1=[O:34]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11]... | CC(C)(C)C(=O)OCCl.CN(C)C=O.O=C([O-])[O-].O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | f327ad19a1c922e995c7d0223df803e824f420c9d5d6ab07e8e1c577caad132f | d87f1657b55388e642bca7fb8eb51bdeb0319bb5f9cfea8f6428b86809fd321a | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[CH3;D1;+0:8].O=[CH;D2;+0:9]-N(-[CH3;D1;+0:10])-[CH3;D1;+0:11].[C:12]-[#7;a:13]1:[c:14]:[#7;a:15]:[c:16]2:[nH;D2;+0:17]:[c:18](=[O;D1;H0:19]):[nH;D2;+0:20]:[c:21](=[O;D1;H0:22]):[c:23]:1:2.[O-;H0;D1:24]-[C;H0;D3;+0:25](-[O-])=[O;D1;H... | null | [] | 50 | CELSIUS | 8 | HOUR | 7-Benzylxanthine (9.54 g) was dissolved in N,N-dimethylformamide (250 ml), and potassium carbonate (17 g) and chloromethyl pivalate (14.2 ml) were added thereto. The reaction solution was stirred at 50° C. overnight, then diluted with ethyl acetate, and washed with water and 1 N hydrochloric acid. The organic layer was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Tertiary amide | Ester.Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | Other | C(C)(=O)OCC | 50 | 8 | CC(C)(C)C(=O)OCCl.CN(C)C=O.O=C([O-])[O-].O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>C(C)(=O)OCC>CC(C)(C)C(=O)OCn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4a90c7c140f43328001ab3d3bb2f0c5 | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2Cl)CC1>>CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1 | N12CCCCCC2=NCCC1.C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O | CC(C)(C)C(=O)OC[n:15]1[c:14]2[n:13][c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:39][CH2:38]3)[n:30](-[c:31]3[cH:32][cH:33][cH:34][cH:35][c:36]3[Cl:37])[c:29]2[c:27](=[O:28])[n:18]([CH2:19][O:20][C:21](=[O:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[c:16]1=[O:17]>>[CH3:1][C:2]([CH... | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2Cl)CC1 | CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1 | null | null | O1CCCC1.CO | Reduction | OtherReaction | 411d41977328c8cadbdefdb39518788b275d2466b65315d3a81f60c385033092 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5](-[c:6]):[c:7]:2:[c:8]:[#7;a:9](-[C:10]):[c:11]:1=[O;D1;H0:12]>>[C:10]-[#7;a:9]1:[c:8]:[c:7]2:[#7;a:5](-[c:6]):[c:4]:[#7;a:3]:[c:2]:2:[nH;D2;+0:1]:[c:11]:1=[O;D1;H0:12] | 55.4 | [{"value": 55.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[7-(2-Chlorophenyl)-1,3-bis-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (2.227 g) was dissolved in tetrahydrofuran (10 ml) and methanol (20 ml), and 1,8-diazabicyclo[5,4,0]undec-7-ene (0.518 ml) was added thereto. The reaction mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1C[NH]CC[NH]1.c1ncc2nc[nH]c2n1.c1ccccc1 | HO- | O1CCCC1.CO | null | 8 | CC(C)(C)OC(=O)N1CCN(c2nc3c(c(=O)n(COC(=O)C(C)(C)C)c(=O)n3COC(=O)C(C)(C)C)n2-c2ccccc2Cl)CC1>O1CCCC1.CO>CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0fc3c0473620495092f8d450da25bdf6 | CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1.COC(=O)CBr>>COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | C(C)(=O)OCC.BrCC(=O)OC.C([O-])([O-])=O.[K+].[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O)CC(=O)OC | [nH:6]1[c:7](=[O:8])[n:9]([CH2:10][O:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[c:18](=[O:19])[c:20]2[c:21]1[n:22][c:23]([N:24]1[CH2:25][CH2:26][N:27]([C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][CH2:36]1)[n:37]2-[c:38]1[cH:39][cH:40][cH:41][cH:42][c:43]1[Cl:44].Br[CH2:5][C:3]([O:2][CH3:1... | CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1.COC(=O)CBr | COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[c:11]):[c:12]:[#7;a:13]:[c:14]:2:[nH;D2;+0:15]:[c:16]:1=[O;D1;H0:17]>>[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[c:11]):[c:12]:[#7;a:13]:[c:14]:2:[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:16]:1... | null | [] | null | null | 8 | HOUR | 4-[7-(2-Chlorophenyl)-1-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (107 mg) was dissolved in N,N-dimethylformamide (2 ml), and methyl bromoacetate (0.025 ml) and potassium carbonate (50 mg) were added to the solution. Then, the mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | CN(C=O)C | null | 8 | CC(C)(C)OC(=O)N1CCN(c2nc3[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c3n2-c2ccccc2Cl)CC1.COC(=O)CBr>CN(C=O)C>COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87358a15c1744a2588d9a9fcb071b59b | COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | [H-].[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)COC(C(C)(C)C)=O)=O)CC(=O)OC.Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)CC(=O)OC | CC(C)(C)C(=O)OC[n:9]1[c:7](=[O:8])[n:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:13]2[c:12]([c:10]1=[O:11])[n:29](-[c:30]1[cH:31][cH:32][cH:33][cH:34][c:35]1[Cl:36])[c:15]([N:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1)[n:14]2>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c... | COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | null | null | O1CCCC1.CO | Reduction | OtherReaction | 15f0619d47e85f67d3db05c38f15a5e9a65c9aacaa3d9463ca5ccdfd111c7722 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]2:[#7;a:5](-[c:6]):[c:7]:[#7;a:8]:[c:9]:2:[#7;a:10](-[C:11]-[C:12](-[#8:13])=[O;D1;H0:14]):[c:15]:1=[O;D1;H0:16]>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]-[#7;a:10]1:[c:9]2:[#7;a:8]:[c:7]:[#7;a:5](-[c:6]):[c:4]:2:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:15]:1=[O;D1;... | 87.8 | [{"value": 87.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-[7-(2-Chlorophenyl)-1-(2,2-dimethylpropionyloxymethyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (139 mg) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and sodium hydride (10 mg) was added to the solution. Then, the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O1CCCC1.CO | null | 1 | COC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>O1CCCC1.CO>COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b986c9c794964f64b10a4786497adfc1 | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)CC(=O)OC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.COC(CN1C(N(C(C=2N(C(=NC12)N1CCNCC1)C1=C(C=CC=C1)Cl)=O)C)=O)=O | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([c:16]2[n:15][c:14]3[n:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:7](=[O:8])[n:9]([CH3:10])[c:11](=[O:12])[c:13]3[n:23]2-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[Cl:30])[CH2:22][CH2:21]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[n:9]([CH3:10])[c:11](=[O:12])[c:13]2[c... | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 4-[7-(2-Chlorophenyl)-3-methoxycarbonylmethyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (26 mg) was dissolved in trifluoroacetic acid, and concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 8.09 mg of the title ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ncc2nc[nH]c2n1.C1C[NH]CCN1.c1ccccc1 | HO- | null | null | null | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCNCC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d62a16b46a5b436791db6b90bf932770 | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C=C=O)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)CC(=O)OC.[OH-].[Na+].Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)C=C=O | CO[C:32]([CH2:31][n:30]1[c:6]2[c:5]([c:3](=[O:4])[n:2]([CH3:1])[c:34]1=[O:35])[n:22](-[c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[Cl:29])[c:8]([N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1)[n:7]2)=[O:33]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2... | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C=C=O)c1=O | null | null | CO | Functional Group Interconversion | OtherReaction | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[#7;a:4](:[c:5]:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]>>[#7;a:10]:[c:9]:[c:7](:[#7;a:8]):[#7;a:4](-[CH;D2;+0:3]=[C;H0;D2;+0:1]=[O;D1;H0:2]):[c:5]:[#7;a:6] | null | [] | null | null | 2 | HOUR | 4-[7-(2-Chlorophenyl)-3-methoxycarbonylmethyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (87 mg) was dissolved in methanol (2 ml), and 5N aqueous sodium hydroxide solution (0.2 ml) was added to the solution. Then, the mixture was stirred at room temperature for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CO | null | 2 | COC(=O)Cn1c(=O)n(C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>CO>Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(C=C=O)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f6ded5d4a094ef798bf89f556b1e2b4 | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O>>Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)C)=O)CC(=O)O.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.ClC1=C(C=CC=C1)N1C(=NC=2N(C(N(C(C12)=O)C)=O)CC(=O)O)N1CCNCC1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([c:8]2[n:7][c:6]3[c:5]([c:3](=[O:4])[n:2]([CH3:1])[c:28](=[O:29])[n:23]3[CH2:24][C:25](=[O:26])[OH:27])[n:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[CH2:14][CH2:13]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[... | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O | Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | 4-[7-(2-Chlorophenyl)-3-carboxymethyl-1-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (26 mg) was dissolved in trifluoroacetic acid, and was concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 10.73 mg of the title com... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ncc2nc[nH]c2n1.C1C[NH]CCN1.c1ccccc1 | HO- | null | null | null | Cn1c(=O)c2c(nc(N3CCN(C(=O)OC(C)(C)C)CC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O>>Cn1c(=O)c2c(nc(N3CCNCC3)n2-c2ccccc2Cl)n(CC(=O)O)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-068de5c6bb6546b196ee2889b2c3e013 | BrCCc1ccccc1.COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>>COC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1C1=C(C=CC=C1)Cl)=O)=O)CC(=O)OC.C([O-])([O-])=O.[K+].[K+].C1=CC=C(C=C1)CCBr>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1C1=C(C=CC=C1)Cl)=O)CCC1=CC=CC=C1)=O)CC(=O)OC | Br[CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[nH:9][c:18](=[O:19])[c:20]2[c:21]1[n:22][c:23]([N:24]1[CH2:25][CH2:26][N:27]([C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][CH2:36]1)[n:37]2-[c:38]1[cH:39][cH:40][cH:41][cH:42][c:43]1[Cl:4... | BrCCc1ccccc1.COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | COC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2nc(N3CCNCC3)n(-c3ccccc3)c2c(=O)n1CCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12](-[c:13]):[c:14]:2:[c:15](=[O;D1;H0:16]):[nH;D2;+0:17]:[c:18]:1=[O;D1;H0:19]>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12](-[c:13]):[c:14]:2:[c:15](=[O;D1;H0:16]):[n;H0;D3;+0:17](-[CH... | null | [] | 50 | CELSIUS | 8 | HOUR | 4-[7-(2-Chlorophenyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (49 mg) was dissolved in N,N-dimethylformamide (1 ml), and potassium carbonate (20 mg) and 2-phenethyl bromide (0.03 ml) were added to the solution. Then, the mixture was stirred at 50°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | CN(C=O)C.C(C)(=O)OCC | 50 | 8 | BrCCc1ccccc1.COC(=O)Cn1c(=O)[nH]c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl>CN(C=O)C.C(C)(=O)OCC>COC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2-c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e6f7aa19885484f959104b2374be228 | CC(C)(C)C(=O)OCCl.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>>CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | C(C1=CC=CC=C1)N1C=NC=2NC(NC(C12)=O)=O.[H-].[Na+].C(C(C)(C)C)(=O)OCCl>>C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)COC(C(C)(C)C)=O | Cl[CH2:8][O:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[nH:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[c:15]2[c:16]1[n:17][cH:18][n:19]2[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11])[nH:12][c:13](=[O:14])[c:15]2[c:16]1[n:17][cH:18][n:19]... | CC(C)(C)C(=O)OCCl.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[nH;D2;+0:11]:[c:12](=[O;D1;H0:13]):[#7;a:14]:[c:15]:[c:16]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[c:16]:1:[c:15]:[#7;a:14]:[c:12](=[O;D1;H0:13]):[n;H0;D3;+0:11]:2-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5] | null | [] | null | null | 8 | HOUR | 7-Benzylxanthine (8.66 g) was dissolved in N,N-dimethylformamide (300 ml); sodium hydride (1.57 g) and chloromethyl pivalate (7.7 ml) were added to the solution; and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and washed with water and 1N hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC(C)(C)C(=O)OCCl.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>CN(C=O)C.C(C)(=O)OCC>CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f381f558a9f34260820e392f41385c6b | CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1.CI>>Cn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)COC(C(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].IC>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)COC(C(C)(C)C)=O | [nH:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]([CH2:18][O:19][C:20](=[O:21])[C:22]([CH3:23])([CH3:24])[CH3:25])[c:26]1=[O:27].I[CH3:1]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]([CH2:18][... | CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1.CI | Cn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 704cb23709e5098e1a572b011399e72714970c743e83535f4ef96273fa60f58e | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | I-[CH3;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c:12](=[O;D1;H0:13]):[c:14]:1:2>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]):[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH3;D1;+0:1]):[c:12](=[O;D1;H0:13]):[c:14]:1:2 | 78.1 | [{"value": 78.1, "product": "C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)C)=O)COC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2,2-Dimethylpropionic Acid [7-benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.66 g) was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (1.6 g) and iodomethane (1 ml) were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted wit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HI | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1.CI>CN(C=O)C.C(C)(=O)OCC>Cn1c(=O)c2c(ncn2Cc2ccccc2)n(COC(=O)C(C)(C)C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-375bbb219b1e45e280b6eb86b75a52a1 | CC#CCBr.Cn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O>>CC#CCn1cnc2c1c(=O)n(C)c(=O)n2COC(=O)C(C)(C)C | CN1C(N(C=2N=CNC2C1=O)COC(C(C)(C)C)=O)=O.C([O-])([O-])=O.[K+].[K+].C(C#CC)Br>>C(C#CC)N1C=NC=2N(C(N(C(C12)=O)C)=O)COC(C(C)(C)C)=O | Br[CH2:4][C:3]#[C:2][CH3:1].[nH:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH3:13])[c:14](=[O:15])[n:16]2[CH2:17][O:18][C:19](=[O:20])[C:21]([CH3:22])([CH3:23])[CH3:24]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH3:13])[c:14](=[O:15])[n:16]2[CH2:17][O:18][C:19](=[O:20])[C:21]([... | CC#CCBr.Cn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O | CC#CCn1cnc2c1c(=O)n(C)c(=O)n2COC(=O)C(C)(C)C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4].[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10](=[O;D1;H0:11]):[c:12]2:[nH;D2;+0:13]:[c:14]:[#7;a:15]:[c:16]:1:2>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10](=[O;D1;H0:11]):[c:12]2:[c:16]:1:[#7;a:15]:[c:14]:[n;H0;D3;+0:13]:2-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4] | null | [] | null | null | 8 | HOUR | 2,2-Dimethylpropionic acid [1-methyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (1.871 g) was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g) and 2-butynyl bromide (0.7 ml) were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC#CCBr.Cn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O>CN(C=O)C.C(C)(=O)OCC>CC#CCn1cnc2c1c(=O)n(C)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd295e1eb51349869bd96a72eccdf9bd | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl>>CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O | CC(C(=O)OCN1C(N(C(C=2NC=NC12)=O)COC(C(C)(C)C)=O)=O)(C)C.ClN1C(CCC1=O)=O>>ClC1=NC=2N(C(N(C(C2N1)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[nH:13][cH:14][n:16][c:17]2[n:18]([CH2:19][O:20][C:21](=[O:22])[C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]1=[O:28].O=C1CCC(=O)N1[Cl:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[nH:13][c:14]([Cl:1... | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl | CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | dfc8035b9f4442cdf7ad3396de3c616a20086152342f560e0286a40409232788 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]1:[#7;a:4]:[cH;D2;+0:5]:[#7;a:6]:[c:7]:1:[c:8]:[#7;a:9]>>[#7;a:2]:[c:3]1:[#7;a:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[#7;a:6]:[c:7]:1:[c:8]:[#7;a:9] | 63.9 | [{"value": 63.9, "product": "ClC1=NC=2N(C(N(C(C2N1)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 2,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (2.31 g) was dissolved in N,N-dimethylformamide (18 ml), and N-chlorosuccinimide (973 mg) was added to the solution while cooling on ice. Then, the mixture was stirred for 10 minutes on ice, and then at ro... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2[nH]cnc2n1.C1CCNC1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 0.166667 | CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O.O=C1CCC(=O)N1Cl>CN(C=O)C.C(C)(=O)OCC>CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-29e4af81ff0c42398af262e4cec2dd03 | CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O.CC(C)=CCBr>>CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | ClC1=NC=2N(C(N(C(C2N1)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].BrCC=C(C)C>>ClC1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | [nH:6]1[c:7]([Cl:8])[n:9][c:10]2[c:11]1[c:12](=[O:13])[n:14]([CH2:15][O:16][C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[c:23](=[O:24])[n:25]2[CH2:26][O:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33].Br[CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][n:6]1[c:7]([Cl:8])[n:9][c:10]2[c:1... | CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O.CC(C)=CCBr | CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11]2:[#7;a:12]:[c:13](-[Cl;D1;H0:14]):[nH;D2;+0:15]:[c:16]:2:[c:17]:1=[O;D1;H0:18]>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11]2:[#7;a:12]:[c:13](-[Cl;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-... | null | [] | null | null | 24 | HOUR | 2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (600 mg) and potassium carbonate (630 mg) were suspended in N,N-dimethylformamide (10 ml), and 4-bromo-2-methyl-2-butene (183 μl) was added to the suspension at room temperature. After the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 24 | CC(C)(C)C(=O)OCn1c(=O)c2[nH]c(Cl)nc2n(COC(=O)C(C)(C)C)c1=O.CC(C)=CCBr>CN(C=O)C.C(C)(=O)OCC>CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-467d5e98194d49c9a3f7f03f8527eb1c | CC(C)(C)OC(=O)N1CCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | ClC1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.C(C)(C)(C)OC(=O)N1CCNCC1.C12=NNCCCC2CCCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.Cl[c:7]1[n:6]([CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[c:23]2[c:22]([n:21]1)[n:37]([CH2:38][O:39][C:40](=[O:41])[C:42]([CH3:43])([CH3:44])[CH3:45])[c:35](=[O:36])[n:26]([CH2:27][O:28][C:29](=[O:30])[C:31]([CH3:32])([CH3:3... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e5786cd15d554d1321f1795004da6d6c939bb0ddb133e8fc80dccdf8a8a64c61 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9]-[C:10]=[C:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]-[C:10]=[C:11]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:16]-[C:17]-[#7:12]-[C:13]-[C:14]-2):[#7;a:2]:[c:3]:1:[#7;a:4] | 45 | [{"value": 45.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 6.5 | HOUR | 2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (470 mg) and 1-piperazinecarboxylic acid tert-butyl ester (218 mg) were dissolved in N-methylpyrrolidone (4 ml), and diazabicyclo[5.4.0]undecene (160 μl) was added to the so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | CN1C(CCC1)=O | 150 | 6.5 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)=CCn1c(Cl)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>CN1C(CCC1)=O>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-66a6c25a85eb44f9b1c4a724bff0a466 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.[H-].[Na+]>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O | CC(C)(C)C(=O)OC[n:23]1[c:22]2[n:21][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]3)[n:6]([CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[c:37]2[c:35](=[O:36])[n:26]([CH2:27][O:28][C:29](=[O:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[c:24]1=[O:25]>>[CH3:1][C:2]([CH3:3])=[CH:... | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | null | null | O1CCCC1.CO.C(C)(=O)OCC | Reduction | OtherReaction | 640a644854d0d424f3b2f603152cc1a7aea1cadf590f863f6706eb0b62b24502 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5](-[C:6]-[C:7]=[C:8]):[c:9]:2:[c:10]:[#7;a:11](-[C:12]):[c:13]:1=[O;D1;H0:14]>>[C:12]-[#7;a:11]1:[c:10]:[c:9]2:[#7;a:5](-[C:6]-[C:7]=[C:8]):[c:4]:[#7;a:3]:[c:2]:2:[nH;D2;+0:1]:[c:13]:1=[O;D1;H0:14] | 94.3 | [{"value": 94.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 4-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (277 mg) was dissolved in a solvent mixture of tetrahydrofuran (3 ml) and methanol (6 ml), sodium hydride (21 mg) was added to the solution, and the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.CO.C(C)(=O)OCC | null | 0.166667 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>O1CCCC1.CO.C(C)(=O)OCC>CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8aa5a0eab0d0486fbd83bdd5e7ac8abf | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr>>CCOC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2CC=C(C)C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC=C(C)C)=O)COC(C(C)(C)C)=O)=O)CC(=O)OCC | [nH:7]1[c:8](=[O:9])[n:10]([CH2:11][O:12][C:13](=[O:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[c:19](=[O:20])[c:21]2[c:22]1[n:23][c:24]([N:25]1[CH2:26][CH2:27][N:28]([C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37]1)[n:38]2[CH2:39][CH:40]=[C:41]([CH3:42])[CH3:43].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])... | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr | CCOC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2CC=C(C)C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[C:11]-[C:12]=[C:13]):[c:14]:[#7;a:15]:[c:16]:2:[nH;D2;+0:17]:[c:18]:1=[O;D1;H0:19]>>[C:6]-[#7;a:7]1:[c:8]:[c:9]2:[#7;a:10](-[C:11]-[C:12]=[C:13]):[c:14]:[#7;a:15]:[c:16]:2:[n;H0;D3;+0:17](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]... | null | [] | null | null | 13 | HOUR | 4-[1-(2,2-Dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (43 mg) and potassium carbonate (13 mg) were suspended in N,N-dimethylformamide (1 ml), and ethyl bromoacetate (9.6 μl) was added to the suspension. After the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1C[NH]CC[NH]1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 13 | CC(C)=CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOC(=O)CBr>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)Cn1c(=O)n(COC(=O)C(C)(C)C)c(=O)c2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)n2CC=C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c2fdca0ce324394835b646a0e3e9743 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O.[H-].[Na+].Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(NC(C2N1CC#CC)=O)=O | CC(C)(C)C(=O)OC[n:22]1[c:21]2[n:20][c:6]([N:7]3[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]3)[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:28]2[c:26](=[O:27])[n:25](COC(=O)C(C)(C)C)[c:23]1=[O:24]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13]... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21 | null | null | O1CCCC1.CO | Reduction | OtherReaction | 4d7c0d1ea9e6438f890ef4cb93fc30107d5f9ce5691b5cd332ff8c75e3907f23 | f8aafe56985277d22343de061be9da73fe4aecbf6a499e356960442d66b98daa | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c:9]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12](-C-O-C(=O)-C(-C)(-C)-C):[c:13]:1=[O;D1;H0:14]>>[C:8]#[C:7]-[C:6]-[#7;a:5]1:[c:4]:[#7;a:3]:[c:2]2:[nH;D2;+0:1]:[c:13](=[O;D1;H0:14]):[nH;D2;+0:12]:[c:10](=[O;D1;H0:11]):[c:9]:1:2 | 100.3 | [{"value": 100.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(NC(C2N1CC#CC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-[7-(2-Butynyl)-1,3-bis-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo 2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (1.9 g) was dissolved in a solvent mixture of tetrahydrofuran (20 ml) and methanol (10 ml), and sodium hydride (0.31 g) was added to the solution. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.CO | null | 1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>O1CCCC1.CO>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-67c84adddfe04c56b3175c19f53c7f99 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.COC(=O)CBr>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(NC(C2N1CC#CC)=O)=O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)CC(=O)OC | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[c:23](=[O:24])[nH:25][c:26](=[O:27])[nH:28]2.Br[CH2:29][C:30](=[O:31])[O:32][CH3:33]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.COC(=O)CBr | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7d358008569a510febb7dbae9ae69699ebd741f56473500303ef0889f4be2b21 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]#[C:7]-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]2:[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[#7;a:16]:[c:17]:[c:18]:1:2>>[C:6]#[C:7]-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]2:[c:18]:1:[c:17]:[#7;a:16]:[c:14](=[O;D1;H0:15]):[n;H0;D3;+0:13]:2-[CH2;D2;+0:1]-[C:2](=[O;D1;... | null | [] | null | null | 8 | HOUR | 4-[7-(2-Butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (50 mg) and potassium carbonate (20 mg) were dissolved in N,N-dimethylformamide (1.5 ml) and methyl bromoacetate (14 μl) was added to the solution while cooling on ice. After the mixture was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.COC(=O)CBr>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d474136064c3418089ffd13c09f942de | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC>>CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)CC(=O)OC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.COC(CN1C(NC(C=2N(C(=NC12)N1CCNCC1)CC#CC)=O)=O)=O | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:15]3[c:14]([n:13]2)[n:21]([CH2:22][C:23](=[O:24])[O:25][CH3:26])[c:19](=[O:20])[nH:18][c:16]3=[O:17])[CH2:12][CH2:11]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][c:14]2[c:15]1[c:16](=[O:17])[... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC | CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 30 | MINUTE | 4-[7-(2-Butynyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (13 mg) was dissolved in trifluoroacetic acid (0.5 ml), and the solution was stirred at room temperature for 30 minutes. After the solvent was removed by distillation, a half of the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | null | null | 0.5 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC>>CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9322b3ac59c4ebe9c338cb97e2c4d5f | CC#CCBr.CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O>>CC#CCn1cnc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | CC(C(=O)OCN1C(N(C(C=2NC=NC12)=O)COC(C(C)(C)C)=O)=O)(C)C.BrCC#CC.C([O-])([O-])=O.[K+].[K+]>>C(C#CC)N1C=NC=2N(C(N(C(C12)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O | Br[CH2:4][C:3]#[C:2][CH3:1].[nH:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][O:14][C:15](=[O:16])[C:17]([CH3:18])([CH3:19])[CH3:20])[c:21](=[O:22])[n:23]2[CH2:24][O:25][C:26](=[O:27])[C:28]([CH3:29])([CH3:30])[CH3:31]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][O:14... | CC#CCBr.CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O | CC#CCn1cnc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4].[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C:9]):[c:10]2:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:[c:15]:1=[O;D1;H0:16]>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C:9]):[c:10]2:[#7;a:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]#[C:3]-[C;D1;H3:4]):[c:14]:2:[c:15]:1=[O;D1;H0:16] | null | [] | null | null | 2 | HOUR | A mixture of 2,2-dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (1.0 g), 1-bromo-2-butyne (0.28 ml), anhydrous potassium carbonate (0.73 g), and N,N-dimethylformamide (15 ml) was stirred at room temperature for 2 hours. The reaction mixture was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C | null | 2 | CC#CCBr.CC(C)(C)C(=O)OCn1c(=O)c2[nH]cnc2n(COC(=O)C(C)(C)C)c1=O>CN(C=O)C>CC#CCn1cnc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bda9e784fbac450ea84836ed4967b311 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O)COC(C(C)(C)C)=O>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O | CC(C)(C)C(=O)OC[n:22]1[c:21]2[n:20][c:6]([N:7]3[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]3)[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:36]2[c:34](=[O:35])[n:25]([CH2:26][O:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[c:23]1=[O:24]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6](... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 | null | null | O1CCCC1.C12=NNCCCC2CCCC1.CO | Reduction | OtherReaction | 640a644854d0d424f3b2f603152cc1a7aea1cadf590f863f6706eb0b62b24502 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]2:[#7;a:3]:[c:4]:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c:9]:2:[c:10]:[#7;a:11](-[C:12]):[c:13]:1=[O;D1;H0:14]>>[C:12]-[#7;a:11]1:[c:10]:[c:9]2:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c:4]:[#7;a:3]:[c:2]:2:[nH;D2;+0:1]:[c:13]:1=[O;D1;H0:14] | 56.5 | [{"value": 56.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[7-(2-Butynyl)-1,3-bis-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (0.63 g) was dissolved in a solvent mixture of tetrahydrofuran (4 ml) and methanol (2 ml), and diazabicyclo[5.4.0]undecene (0.18 ml) was added to the solution. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.C12=NNCCCC2CCCC1.CO | null | 8 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2COC(=O)C(C)(C)C>O1CCCC1.C12=NNCCCC2CCCC1.CO>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a041411423e04062a5fddfda39e9c96d | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOCCBr>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O.C([O-])([O-])=O.[K+].[K+].BrCCOCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O)CCOCC | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[c:23](=[O:24])[n:25]([CH2:26][O:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[c:34](=[O:35])[nH:36]2.Br[CH2:37][CH2:38][O:39][CH2:40][CH3:41]>>[CH3:1][C:... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOCCBr | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[#7;a:5]1:[c:6]:[c:7]2:[#7;a:8](-[C:9]-[C:10]#[C:11]):[c:12]:[#7;a:13]:[c:14]:2:[nH;D2;+0:15]:[c:16]:1=[O;D1;H0:17]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:15]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:8](-[C:9]-[C:10]#[C:11]):[c:7]:2:[c:6]:[#7;a:5](-[C:4]):[c:16]:1=[O;D1;H0:17] | null | [] | 60 | CELSIUS | 2 | HOUR | 4-[7-(2-Butynyl)-1-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (50 mg) and potassium carbonate (15 mg) were dissolved in N,N-dimethylformamide (1.2 ml), and 2-bromoethylethyl ether (12 μl) was added to the solution. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | 60 | 2 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)n(COC(=O)C(C)(C)C)c(=O)c21.CCOCCBr>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d0433592edf4ea68c54e448264df983 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)COC(C(C)(C)C)=O)=O)CCOCC.[H-].[Na+].Cl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)CCOCC | CC(C)(C)C(=O)OC[n:25]1[c:23](=[O:24])[c:22]2[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:6]([N:7]3[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]3)[n:20][c:21]2[n:28]([CH2:29][CH2:30][O:31][CH2:32][CH3:33])[c:26]1=[O:27]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC | null | null | O1CCCC1.CO | Reduction | OtherReaction | df8a3c8b7aa7d10b48c9fb6d61e80538577be49615529cea0e9d9fc23715d092 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]2:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c:9]:[#7;a:10]:[c:11]:2:[#7;a:12](-[C:13]):[c:14]:1=[O;D1;H0:15]>>[C:13]-[#7;a:12]1:[c:11]2:[#7;a:10]:[c:9]:[#7;a:5](-[C:6]-[C:7]#[C:8]):[c:4]:2:[c:2](=[O;D1;H0:3]):[nH;D2;+0:1]:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | 1 | HOUR | 4-[7-(2-Butynyl)-1-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (50 mg) and potassium carbonate (15 mg) were dissolved in N,N-dimethylformamide (1.2 ml), and 2-bromoethylethyl ether (12 μl) was added to the solution. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HO- | O1CCCC1.CO | null | 1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(COC(=O)C(C)(C)C)c(=O)n2CCOCC>O1CCCC1.CO>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ecbda20c6b14eb28c62e1fdcf3b27a7 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC>>CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CCOCC | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)CCOCC.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.C(C#CC)N1C(=NC=2N(C(NC(C12)=O)=O)CCOCC)N1CCNCC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:15]3[c:14]([n:13]2)[n:21]([CH2:22][CH2:23][O:24][CH2:25][CH3:26])[c:19](=[O:20])[nH:18][c:16]3=[O:17])[CH2:12][CH2:11]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][c:14]2[c:15]1[c:16](=[O:17])... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC | CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CCOCC | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 30 | MINUTE | 4-[7-(2-Butynyl)-1-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (50 mg) and potassium carbonate (15 mg) were dissolved in N,N-dimethylformamide (1.2 ml), and 2-bromoethylethyl ether (12 μl) was added to the solution. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ncc2[nH]cnc2n1 | HO- | null | null | 0.5 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2CCOCC>>CC#CCn1c(N2CCNCC2)nc2c1c(=O)[nH]c(=O)n2CCOCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb1d316206cb4395ac0d259040c7c242 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.CC(C)(C)C(=O)OCCl>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2NC(NC(C2N1CC#CC)=O)=O.C([O-])([O-])=O.[K+].[K+].C(C(C)(C)C)(=O)OCCl>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)COC(C(C)(C)C)=O | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[c:23](=[O:24])[nH:25][c:26](=[O:27])[nH:28]2.Cl[CH2:29][O:30][C:31](=[O:32])[C:33]([CH3:34])([CH3:35])[CH3:36]>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.CC(C)(C)C(=O)OCCl | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7d358008569a510febb7dbae9ae69699ebd741f56473500303ef0889f4be2b21 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[C:6]#[C:7]-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]2:[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[#7;a:16]:[c:17]:[c:18]:1:2>>[C:6]#[C:7]-[C:8]-[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]2:[c:18]:1:[c:17]:[#7;a:16]:[c:14](=[O;D1;H0:15]):[n;H0;D3;+0:13]:2-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4]... | null | [] | null | null | 8 | HOUR | 4-[7-(2-Butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (1.1 g) and potassium carbonate (0.43 g) were dissolved in N,N-dimethylformamide (15 ml), and chloromethyl pivalate (0.60 ml) was added to the solution while cooling on ice. After the mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2[nH]c(=O)[nH]c(=O)c21.CC(C)(C)C(=O)OCCl>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7df419ff47744b5ab04a53aa0e3b9153 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C.CCOCCBr>>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCOCC)c(=O)n2COC(=O)C(C)(C)C | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(NC(C2N1CC#CC)=O)=O)COC(C(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].BrCCOCC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=NC=2N(C(N(C(C2N1CC#CC)=O)CCOCC)=O)COC(C(C)(C)C)=O | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[c:23](=[O:24])[nH:25][c:31](=[O:32])[n:33]2[CH2:34][O:35][C:36](=[O:37])[C:38]([CH3:39])([CH3:40])[CH3:41].Br[CH2:26][CH2:27][O:28][CH2:29][CH3:30]>>[CH3:1][C:2]... | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C.CCOCCBr | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCOCC)c(=O)n2COC(=O)C(C)(C)C | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]c(N3CCNCC3)nc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]#[C:5]-[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:15]1:[c:16](=[O;D1;H0:17]):[c:18]2:[#7;a:7](-[C:6]-[C:5]#[C:4]):[c:8]:[#7;a:9]:[c:10]:2:[#7;a:11](-[C:12]):[c:1... | null | [] | 60 | CELSIUS | 5 | HOUR | 4-[7-(2-Butynyl)-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (40 mg) and potassium carbonate (17 mg) were dissolved in N,N-dimethylformamide (1.5 ml), and 2-bromoethylethyl ether (14 μl) was added to the solution. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1C[NH]CC[NH]1.c1ncc2[nH]cnc2n1 | HBr | CN(C=O)C.C(C)(=O)OCC | 60 | 5 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)[nH]c(=O)n2COC(=O)C(C)(C)C.CCOCCBr>CN(C=O)C.C(C)(=O)OCC>CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2c1c(=O)n(CCOCC)c(=O)n2COC(=O)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b79b7d05e904ad699295bfc2c1e43f1 | CCOC(=O)CBr.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>>CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | BrCC(=O)OCC.C(C1=CC=CC=C1)N1C=NC=2NC(NC(C12)=O)=O.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>C(C)OC(CN1C(NC(C=2N(C=NC12)CC1=CC=CC=C1)=O)=O)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[c:8](=[O:9])[nH:10][c:11](=[O:12])[c:13]2[c:14]1[n:15][cH:16][n:17]2[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[nH:10][c:11](=[O:12])[c:13]2[c:14]1[n:15][cH:16][n:17]2[CH2:18][c:19]1[cH:20][cH:21][cH:22... | CCOC(=O)CBr.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 26fc3bf60932ac03263e5db4befaff6206b78a6737a803bc4f7a9443b30c22c1 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[nH;D2;+0:11]:[c:12](=[O;D1;H0:13]):[#7;a:14]:[c:15]:[c:16]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[c:16]:1:[c:15]:[#7;a:14]:[c:12](=[O;D1;H0:13]):[n;H0;D3;+0:11]:2-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | 44.1 | [{"value": 44.1, "product": "C(C)OC(CN1C(NC(C=2N(C=NC12)CC1=CC=CC=C1)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | A mixture of 7-benzyl-3,7-dihydropurine-2,6-dione (3.0 g), anhydrous potassium carbonate (2.0 g), and N,N-dimethylformamide (60 ml) was stirred with heating in an oil bath of 40° C., and ethyl bromoacetate (1.5 g) was added thereto. The mixture was stirred by heating at the same temperature for 4 hours. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | O.C(C)(=O)OCC | 40 | null | CCOC(=O)CBr.O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1>O.C(C)(=O)OCC>CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2c0009f640dc46d3afe7c01413d3ef10 | BrCCc1ccccc1.CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1ncn2Cc1ccccc1 | C(C)OC(CN1C(NC(C=2N(C=NC12)CC1=CC=CC=C1)=O)=O)=O.C([O-])([O-])=O.[K+].[K+].BrCCC1=CC=CC=C1.CN(C=O)C>>C(C)OC(CN1C(N(C(C=2N(C=NC12)CC1=CC=CC=C1)=O)CCC1=CC=CC=C1)=O)=O | Br[CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[nH:10][c:19](=[O:20])[c:21]2[c:22]1[n:23][cH:24][n:25]2[CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[c:8](=[O:9])[n:10]([CH2:11][CH2:12][c:13]2[cH... | BrCCc1ccccc1.CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1ncn2Cc1ccccc1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ncn(Cc3ccccc3)c2c(=O)n1CCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12](-[C:13]):[c:14]:2:[c:15](=[O;D1;H0:16]):[nH;D2;+0:17]:[c:18]:1=[O;D1;H0:19]>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7;a:8]1:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12](-[C:13]):[c:14]:2:[c:15](=[O;D1;H0:16]):[n;H0;D3;+0:17](-[CH... | null | [] | 50 | CELSIUS | null | null | A mixture of (7-benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl)acetic acid ethyl ester (300 mg), anhydrous potassium carbonate (250 mg), 2-bromoethylbenzene (0.25 ml), and N,N-dimethylformamide (5 ml) was stirred with heating in an oil bath of 50° C. for 2 hours. The reaction mixture was diluted with ethyl acetate and w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | O.C(C)(=O)OCC | 50 | null | BrCCc1ccccc1.CCOC(=O)Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>O.C(C)(=O)OCC>CCOC(=O)Cn1c(=O)n(CCc2ccccc2)c(=O)c2c1ncn2Cc1ccccc1 |
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