dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52fd8741bb834006b358fce63495c8d0 | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1OC | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:26][c:27]1[O:28][CH3:29].Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4... | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3,4-dimethoxyaniline were reacted to yield N2-(3,4-dimethoxyphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. LCM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19813ace2dea4bec80cf1c0ebd1f1d2b | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)c(Cl)c1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC=1C=C(N)C=CC1F>>ClC=1C=C(C=CC1F)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[O:20][CH2:21][CH2:22][O:23]3)[n:24]1.[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:25][c:26]1[Cl:27]>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)c(Cl)c1 | Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-chloro-4-fluoroaniline were reacted to yield N2-(3-chloro-4-fluorophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)c(Cl)c1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-927f61f8c6f94712b7395cc6de348920 | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)(C)(C)C1=CC=C(N)C=C1>>C(C)(C)(C)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:28][cH:29]1.Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[O:23][CH2:24][CH2:25][O:26]3)[n:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][... | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-tert-butylaniline were reacted to yield N2-(4-tert-butylphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-187c96537c5a42148791928898039b69 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)cc1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC1=CC=C(N)C=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)F | Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[O:20][CH2:21][CH2:22][O:23]3)[n:24]1.[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:25][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][CH2:21... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)cc1 | Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-fluoroaniline were reacted to yield N4-(3,4-ethylenedioxyphenyl)-N2-(4-fluorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(F)cc1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbf56aceee7c4a7bb6cf6caecaf92b4c | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(F)c1>>Fc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC=1C=C(N)C=CC1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)F | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21]... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(F)c1 | Fc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-fluoroaniline were reacted to yield N4-(3,4-ethylenedioxyphenyl)-N2-(3-fluorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(F)c1>>Fc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1a9d915fc1340bcadafef6db78a8f72 | COCCN.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COCCN>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NCCOC | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[O:19][CH2:20][CH2:21][O:22]3)[n:23]1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[O:19][CH2:20][CH2:21][O:22]3)[n:23]1 | COCCN.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)OCCO3)ncn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-methoxyethylamine were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-methoxyethyl)-2,4-pyrimidinediamine. 1H NMR (C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COCCN.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a2d0f12d4ed482c98fe3f332f4d5c44 | COc1ccc(CN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(CNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC1=CC=C(CN)C=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NCC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:27][cH:28]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:1... | COc1ccc(CN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(CNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-methoxybenzylamine were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(4-methoxybenzyl)-2,4-pyrimidinediamine. 1H NMR ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(CN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(CNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24095a4694e7424caee45e21438dd464 | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2[nH]1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)OC(=O)C=1NC2=CC=C(C=C2C1)N>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:30][cH:31][c:32]2[nH:33]1.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][cH:21][c:22]3[c:23]([cH:24]2)[O:25][CH2:26][CH2:27][O:28]3)[n:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[n:13][c... | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3[nH]ccc3c2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-ethoxycarbonyl-5-aminoindole were reacted to yield N2-(2-ethoxycarbonylindol-5-yl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrim... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dbd7090da43441fb081d5a4c928fff5 | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)OC(=O)C=1C=C(N)C=CC1>>C(C)OC(=O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:30]1.Oc1cccc(N[c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]4[c:23]([cH:24]3)[O:25][CH2:26][CH2:27][O:28]4)[n:29]2)c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]... | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-ethoxycarbonylaniline gave N2-(3-ethoxycarbonylphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2dd2de9b9fd743d39ac4d7e41934f37e | NCCO.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>OCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.OCCN>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NCCO | [OH:1][CH2:2][CH2:3][NH2:4].Oc1cccc(N[c:5]2[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[O:18][CH2:19][CH2:20][O:21]4)[n:22]2)c1>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[O:18][CH2:19][CH2:20][O:21]3)[n:22]1 | NCCO.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | OCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)ncn1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-hydroxyethylamine gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydroxyethyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.7 (bs, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | NCCO.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>OCCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-375483a704a74f75b5e61e31904745c4 | Cc1cc(N)cc(Cl)c1O.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Cc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(Cl)c1O | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC=1C=C(N)C=C(C1O)C>>ClC=1C=C(C=C(C1O)C)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:21][c:22]([Cl:23])[c:24]1[OH:25].Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]2)[n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]3)[n:20]2)[cH:21][... | Cc1cc(N)cc(Cl)c1O.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Cc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(Cl)c1O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-chloro-4-hydroxy-5-methylaniline gave N2-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Cc1cc(N)cc(Cl)c1O.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Cc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(Cl)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77aab961867a49f59934e7de5e9abf76 | Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O.Nc1cccc(O)c1>>Cc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(Cl)c1O | ClC1=NC=C(C(=N1)NC1=CC(=C(C(=C1)C)O)Cl)F.OC=1C=C(N)C=CC1>>ClC=1C=C(C=C(C1O)C)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:8]1[n:7][c:6]([NH:5][c:4]2[cH:3][c:2]([CH3:1])[c:24]([OH:25])[c:22]([Cl:23])[cH:21]2)[c:19]([F:20])[cH:18][n:17]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]3)[n:17][cH:18][c:19]2[F:20])[cH:21][... | Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O.Nc1cccc(O)c1 | Cc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(Cl)c1O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-chloro-4-hydroxy-5-methylphenyl)-4-pyrimidineamine with 3-hydroxyaniline gave N4-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O.Nc1cccc(O)c1>>Cc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(Cl)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1617de8724994c47bd35fe931678997c | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)cc1OC | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCN1CCOCC1)F.COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCN1CCOCC1)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:32][c:33]1[O:34][CH3:35].Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][cH:30]2)[n:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F... | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1 | COc1ccc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc(OCCCN4CCOCC4)cc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-[4-[3-(N-morpholinyl)propyl]oxyphenyl]-4-pyrimidineamine with 3,4-dimethoxyaniline gave N2-(3,4-dimethoxyphenyl)-5-fluoro-N4-[4-[3-(N-morpholinyl)propyl]oxyphenyl]-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.C1COCC[NH]1 | HCl | null | null | null | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2731df9771c344f28b2a40410d69d038 | Cc1cc(N)c(Cl)cc1O.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1>>Cc1cc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)c(Cl)cc1O | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCN1CCOCC1)F.ClC1=C(N)C=C(C(=C1)O)C>>ClC1=C(C=C(C(=C1)O)C)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCN1CCOCC1)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:30]([Cl:31])[cH:32][c:33]1[OH:34].Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[cH:27][cH:28]2)[n:29]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12... | Cc1cc(N)c(Cl)cc1O.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1 | Cc1cc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)c(Cl)cc1O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc(OCCCN4CCOCC4)cc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-[4-[3-(N-morpholinyl)propyl]oxyphenyl]-4-pyrimidineamine with 2-chloro-4-hydroxy-5-methylaniline gave N2-(2-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-N4-[4-[3-(N-mo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.C1COCC[NH]1 | HCl | null | null | null | Cc1cc(N)c(Cl)cc1O.Fc1cnc(Cl)nc1Nc1ccc(OCCCN2CCOCC2)cc1>>Cc1cc(Nc2ncc(F)c(Nc3ccc(OCCCN4CCOCC4)cc3)n2)c(Cl)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3f43d71481347249e5448408fd45c0c | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)Cl.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27]2)[n:28]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](... | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hyroxyphenyl)-2,4-pyrimidinediamine, N4-(3-tert-butylphenyl)-2-chloro-5-fluoro-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to give N4-(3-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee56e6259ba745a594f2f1e32df1ac76 | CC(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)C)c4)n3)ccc2o1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(C)C)F.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)C(C)C | Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26]2)[n:27]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:28][cH:29][c:30]2[o:31]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c... | CC(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)C)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hyroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-isopropylphenyl)-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to give 5-fluoro-N4-(3-isopropylphenyl)-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)c1cccc(Nc2nc(Cl)ncc2F)c1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)C)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0c735e7fdb54b33b9c56e5addf01c44 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1nc(Cl)c(Cl)[nH]1>>Fc1cnc(Nc2ccc(-n3cnc(Cl)c3Cl)cc2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC=1N=C(NC1Cl)N>>ClC=1N=CN(C1Cl)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:21]([NH:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[O:29][CH2:30][CH2:31][O:32]3)[n:20]1.[NH2:6][c:7]1[nH:11][c:16]([Cl:17])[c:8]([Cl:15])[n:13]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10](-[n:11]3[cH:12][n:13][c:14]([Cl:15])[c:16]3[Cl:17])[cH:18][cH:19]2)[n:20][c:... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1nc(Cl)c(Cl)[nH]1 | Fc1cnc(Nc2ccc(-n3cnc(Cl)c3Cl)cc2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2d34500859210fffa4dde1b2217bdbeed7d161e7c4814486383ba7f13aa3c7e8 | 2d0b5393fc929740da65e21b9b211e5c2cba3df38088e77e4a72dcd4889dfe97 | c1cn(-c2ccc(Nc3nccc(Nc4ccc5c(c4)OCCO5)n3)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[Cl;D1;H0:6]-[c;H0;D3;+0:7]1:[nH;D2;+0:8]:[c;H0;D3;+0:9](-[NH2;D1;+0:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[Cl;H0;D1;+0:13]>>[Cl;D1;H0:6]-[c;H0;D3;+0:7]1:[c:14](-[Cl;H0;D1;+0:13]):[n;H0;D2;+0:11]:[c:15]:[n;H0;D3;+0:8]:1-[c:16]1:[c:17]:[c:18]:[c;H0;D3;+0:9](-[NH;D2;+0:1... | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 4,5-dichloro-1H-imidazoleamine gave N2-[4-(4,5-dichloro-1H-imidazol-1-yl)phenyl]-N4-(3,4-ethylenedioxyphenyl)-5-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Secondary amine | c1cncnc1.c1c[nH]cn1 | c1cncnc1.c1ccccc1.c1c[nH]cn1 | c1cncnc1.c1ccccc1.c1c[nH]cn1.c1ccc2c(c1)OCCO2 | null | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1nc(Cl)c(Cl)[nH]1>>Fc1cnc(Nc2ccc(-n3cnc(Cl)c3Cl)cc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc0e9b7271e741ae81a67ce3a01a29b1 | COc1ccc(N)c(OC)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(OC)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC1=C(N)C=CC(=C1)OC>>COC1=C(C=CC(=C1)OC)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:26]([O:27][CH3:28])[cH:29]1.Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18... | COc1ccc(N)c(OC)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 2,4-dimethoxyaniline gave N2-(2,4-dimethoxyphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(N)c(OC)c1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0520f5aa00d4492990d18ca2e82bc03b | CC(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)(C)C1=CC=C(N)C=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:27][cH:28]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:26]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:1... | CC(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CC(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 4-isopropylaniline gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(4-isopropylphenyl)-2,4-pyrimidinediamine. 1H NMR ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CC(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC(C)c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-557ecd1489ff44e0aef11bf841372b2a | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)cc1O | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.CC1=C(N)C=C(C(=C1)O)C>>CC1=C(C=C(C(=C1)O)C)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:24]([CH3:25])[cH:26][c:27]1[OH:28].Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[O:19][CH2:20][CH2:21][O:22]3)[n:23]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[... | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)cc1O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 2,5-dimethyl-4-hydroxyaniline gave N2-(2,5-dimethyl-4-hydroxyphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>Cc1cc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c(C)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15af6caa704742bd91938ceb696c5bf8 | CC1=C(N)N(c2ccccc2)CO1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC1=C(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)N(c2ccccc2)CO1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.CC1=C(N(CO1)C1=CC=CC=C1)N>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1N(COC1C)C1=CC=CC=C1 | [CH3:1][C:2]1=[C:3]([NH2:4])[N:23]([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[CH2:30][O:31]1.Cl[c:5]1[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[O:18][CH2:19][CH2:20][O:21]3)[n:22]1>>[CH3:1][C:2]1=[C:3]([NH:4][c:5]2[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4... | CC1=C(N)N(c2ccccc2)CO1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CC1=C(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)N(c2ccccc2)CO1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 94565f710f99d4155675a9f0732ab870d49a7a93dcea19270d443f9bfa287db3 | ccccfb95b8e69084b65046e8e8e3287b0bbdd155a721ff5e70243e9793e85756 | C1=C(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)N(c2ccccc2)CO1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7]1=[C:8](-[NH2;D1;+0:9])-[#7:10](-[c:11])-[C:12]-[#8:13]-1>>[C;D1;H3:6]-[C:7]1=[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[#7:10](-[c:11])-[C:12]-[#8:13]-1 | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 5-methyl-3-phenyl-4-oxazolylamine gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(5-methyl-3-phenyl-4-oxazolyl)-2,4-... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide | Enamine | c1cncnc1 | c1cncnc1 | C1=COC[NH]1.c1cncnc1.c1ccc2c(c1)OCCO2.c1ccccc1 | HCl | null | null | null | CC1=C(N)N(c2ccccc2)CO1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CC1=C(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)N(c2ccccc2)CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef6e25b55ef943c286d9dd6b81b4258c | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:26][cH:27][c:28]2[o:29]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]2)[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]... | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 2-methoxycarbonyl-5-aminobenzofuran gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-463e54b029c1434a85889cab93f4debb | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C)OC(=O)C=1NC2=CC=C(C=C2C1)N>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH2:11])[cH:27][cH:28][c:29]2[nH:30]1.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][cH:21][cH:22][c:23]([OH:24])[cH:25]2)[n:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[n:13][cH:14][c:15]([F:16])[c:... | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4[nH]ccc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 2-ethoxycarbony-5-aminoindole gave N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a06010e3a1c447359bbf2e65edaa042d | CC(C)c1ccc(N)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CC(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C)(C)C1=CC=C(N)C=C1>>FC=1C(=NC(=NC1)NC1=CC=C(C=C1)C(C)C)NC1=CC(=CC=C1)O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:24][cH:25]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]2)[n:23]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([OH:21... | CC(C)c1ccc(N)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | CC(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 4-isopropylaniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(4-isopropylphenyl)-2,4-pyrimidinediamine. LCMS: ret. time: 23.08 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)c1ccc(N)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>CC(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adca59c615b14532ad41bebb5d6d3fc1 | COc1cc(N)cc(OC)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC=1C=C(N)C=C(C1)OC>>COC=1C=C(C=C(C1)OC)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:22][c:23]([O:24][CH3:25])[cH:26]1.Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]2)[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]3)[n:... | COc1cc(N)cc(OC)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3,5-dimethoxyaniline gave N2-(3,5-dimethoxyphenyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. LCMS: ret. time: 19... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1cc(N)cc(OC)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed3597d717b8438ea49d3b2c5d50df0a | Fc1cnc(Cl)nc1NC(c1ccc(Cl)cc1)c1ccc(Cl)cc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)n2)c1 | NC=1C=C(C=CC1)O.ClC1=NC=C(C(=N1)NC(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH:15]([c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[n:30]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:31]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH:15]([c... | Fc1cnc(Cl)nc1NC(c1ccc(Cl)cc1)c1ccc(Cl)cc1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(NC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(NC(c3ccccc3)c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-4-pyrimidinediamine, 3-aminophenol and N-(2-chloro-5-fluoro-pyrimidinyl)-1,1-di(4-chlorophenyl)methylamine produced 5-fluoro-N2-(3-hydroxyphenyl)-N4-[di-(4-chlorophenyl)methyl]-2,4-pyrimidinediamine. LCMS: ret. time: 25.59 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1NC(c1ccc(Cl)cc1)c1ccc(Cl)cc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5bb75491034475fa4ac7cc10250ea99 | Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NC3c4ccccc4-c4ccccc43)n2)c1 | ClC1=NC=C(C(=N1)NC1C2=CC=CC=C2C=2C=CC=CC12)F.NC=1C=C(C=CC1)O>>C1=CC=CC=2C3=CC=CC=C3C(C12)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH:15]2[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3-[c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]32)[n:28]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:29]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH:15]3[c:16]4[cH:17][cH:1... | Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(NC3c4ccccc4-c4ccccc43)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(NC3c4ccccc4-c4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-4-pyrimidinediamine, 2-chloro-N-(fluoren-9-yl)-5-fluoro-4-pyrimidineamine and 3-aminophenol were reacted to produce N4-(fluoren-9-yl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.85 (d, 1H, J=2.9 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)Cc1ccccc12 | HCl | null | null | null | Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NC3c4ccccc4-c4ccccc43)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6effd5aa7a44aa59aac97b0627e5fdd | CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1.Nc1cccc(O)c1>>CC(Nc1nc(Nc2cccc(O)c2)ncc1F)c1ccc(F)cc1 | NC=1C=C(C=CC1)O.ClC1=NC=C(C(=N1)NC(C)C1=CC=C(C=C1)F)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC(C)C1=CC=C(C=C1)F | Cl[c:6]1[n:5][c:4]([NH:3][CH:2]([CH3:1])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:17]([F:18])[cH:16][n:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]2)[n:15][cH:16][c:17]1[F:18])[c:19]1[cH:20][cH:21][... | CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1.Nc1cccc(O)c1 | CC(Nc1nc(Nc2cccc(O)c2)ncc1F)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-4-pyrimidinediamine, 3-aminophenol and (±)-N-(2-chloro-5-fluoropyrimidinyl)-1-(4-fluorophenyl)ethylamine were reacted to produce the desired (±)-5-fluoro-N4-[1-(4-fluorophenyl)ethyl]-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1.Nc1cccc(O)c1>>CC(Nc1nc(Nc2cccc(O)c2)ncc1F)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d02b71b0d004acf9dbc45c0e09a465a | CC(Nc1nc(Cl)ncc1Br)c1ccc(F)cc1.Nc1cccc(O)c1>>CC(Nc1nc(Nc2cccc(O)c2)ncc1Br)c1ccc(F)cc1 | NC=1C=C(C=CC1)O.BrC=1C(=NC(=NC1)Cl)NC(C)C1=CC=C(C=C1)F>>BrC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC(C)C1=CC=C(C=C1)F | Cl[c:6]1[n:5][c:4]([NH:3][CH:2]([CH3:1])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:17]([Br:18])[cH:16][n:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]2)[n:15][cH:16][c:17]1[Br:18])[c:19]1[cH:20][cH:21... | CC(Nc1nc(Cl)ncc1Br)c1ccc(F)cc1.Nc1cccc(O)c1 | CC(Nc1nc(Nc2cccc(O)c2)ncc1Br)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-4-pyrimidinediamine, 3-aminophenol and (±)-5-bromo-2-chloro-N4-[1-(4-fluorophenyl)ethyl]-4-pyrimidineamine were reacted to produce (±)-5-bromo-N4-[1-(4-fluorophenyl)ethyl]-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(Nc1nc(Cl)ncc1Br)c1ccc(F)cc1.Nc1cccc(O)c1>>CC(Nc1nc(Nc2cccc(O)c2)ncc1Br)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3139ee097a3945838e81f2ab9f6fb21c | Nc1cccc(O)c1.Nc1nc(Cl)ncc1Br>>Nc1nc(Nc2cccc(O)c2)ncc1Br | NC1=NC(=NC=C1Br)Cl.NC=1C=C(C=CC1)O>>NC1=NC(=NC=C1Br)NC1=CC(=CC=C1)O | [NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1.Cl[c:4]1[n:3][c:2]([NH2:1])[c:15]([Br:16])[cH:14][n:13]1>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]2)[n:13][cH:14][c:15]1[Br:16] | Nc1cccc(O)c1.Nc1nc(Cl)ncc1Br | Nc1nc(Nc2cccc(O)c2)ncc1Br | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-4-pyrimidinediamine, 4-amino-5-bromo-2-chloropyrimidine and 3-aminophenol were reacted to give 4-amino-5-bromo-N2-(3-hydroxyphenyl)-2-pyrimidineamine. 1H NMR (DMSO-d6): δ 10.33 (br s, 1H), 8.27 (s, 1H), 7.14-6.06 (m, 2H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Nc1cccc(O)c1.Nc1nc(Cl)ncc1Br>>Nc1nc(Nc2cccc(O)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17ee5d4b21ee47a8bea36834dc6da47d | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(OCC(O)CO)cc1>>OCC(O)COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.OC(COC1=CC=C(N)C=C1)CO>>OC(COC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F)CO | Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][cH:21][c:22]3[c:23]([cH:24]2)[O:25][CH2:26][CH2:27][O:28]3)[n:29]1.[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:30][cH:31]1>>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15](... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(OCC(O)CO)cc1 | OCC(O)COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine and 4-(2,3-dihydroxypropoxy)aniline were reacted to produce N2-[4-(2,3-dihydroxypropoxy)phenyl]-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc(OCC(O)CO)cc1>>OCC(O)COc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25789d6d20634be7990dd2b067ea892e | Nc1ccc(OCC(O)CO)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>OCC(O)COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.OC(COC1=CC=C(N)C=C1)CO>>OC(COC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F)CO | [OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:27][cH:28]1.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][cH:21][cH:22][c:23]([OH:24])[cH:25]2)[n:26]1>>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][... | Nc1ccc(OCC(O)CO)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | OCC(O)COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine and 4-(2,3-dihydroxypropoxy)aniline were reacted to produce N2-[4-(2,3-dihydroxypropoxy)phenyl]-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediami... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Nc1ccc(OCC(O)CO)cc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>OCC(O)COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4221563cbc17452f9a86a086ff2932fb | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.Cc1cc(N)cc(Cl)c1O>>Cc1cc(Nc2ncc(F)c(Nc3cccc(C(C)(C)C)c3)n2)cc(Cl)c1O | C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)Cl.ClC=1C=C(N)C=C(C1O)C>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=C(C(=C1)C)O)Cl | Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]2)[n:23]1.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:24][c:25]([Cl:26])[c:27]1[OH:28]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([F:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([C:18]... | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.Cc1cc(N)cc(Cl)c1O | Cc1cc(Nc2ncc(F)c(Nc3cccc(C(C)(C)C)c3)n2)cc(Cl)c1O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of N4-(3-tert-butylphenyl)-2-chloro-5-fluoro-4-pyrimidineamine with 3-chloro-4-hydroxy-5-methylaniline gave N4-(3-tert-butylphenyl)-N2-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-2,4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)c1cccc(Nc2nc(Cl)ncc2F)c1.Cc1cc(N)cc(Cl)c1O>>Cc1cc(Nc2ncc(F)c(Nc3cccc(C(C)(C)C)c3)n2)cc(Cl)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f4b82a5c0384cd2be96d3b720f85be8 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(C(F)(F)F)c1>>Fc1cnc(Nc2cccc(C(F)(F)F)c2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.FC(C=1C=C(N)C=CC1)(F)F>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)C(F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[n:17]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[n:17][c:18... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(C(F)(F)F)c1 | Fc1cnc(Nc2cccc(C(F)(F)F)c2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 3-trifluoromethylaniline gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-trifluoromethylphenyl)-2,4-pyrimidinediam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(C(F)(F)F)c1>>Fc1cnc(Nc2cccc(C(F)(F)F)c2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fddcdbdc4124472baa6d264a43f1c8fb | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2cnco2)c1>>Fc1cnc(Nc2cccc(-c3cnco3)c2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.O1C=NC=C1C=1C=C(N)C=CC1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)C1=CN=CO1 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:19]([NH:20][c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][CH2:29][O:30]3)[n:18]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][n:14][cH:15][o:16]2)[cH:17]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][n:14][cH:15][o:16]3)[cH:17... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2cnco2)c1 | Fc1cnc(Nc2cccc(-c3cnco3)c2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc(-c2cnco2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 3-(1,3-oxazol-5-yl)aniline gave N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(1,3-oxazol-5-yl)phenyl]-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1cocn1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(-c2cnco2)c1>>Fc1cnc(Nc2cccc(-c3cnco3)c2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d59328c12a2a41e7a5f7b60b2734e207 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(N)c1>>Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)Cl.NC=1C=C(N)C=CC1>>NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1.[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(N)c1 | Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | 70 | CELSIUS | null | null | N4-(3,4-Ethylenedioxyphenyl)-2-chloro-5-fluoro-4-pyrimidineamine (50 mg, 0.18 mmol) was dissolved in dry MeOH (1 ml), to it was added 3-aminoaniline (163 mg, 1.2 mmol) and the mixture was refluxed for 4 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | CO | 70 | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(N)c1>CO>Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54651f1f17be4937a02b2bcbd466b92b | COC(=O)c1cc2cc(N)ccc2o1.Nc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(N)c4)n3)ccc2o1 | NC=1C=C(C=CC1)NC1=NC(=NC=C1F)Cl.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>NC=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:26][cH:27][c:28]2[o:29]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([NH2:23])[cH:24]2)[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18... | COC(=O)c1cc2cc(N)ccc2o1.Nc1cccc(Nc2nc(Cl)ncc2F)c1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(N)c4)n3)ccc2o1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A mixture of N4-(3-aminophenyl)-2-chloro-5-fluoro-4-pyrimidineamine (10 mg, 0.06 mmol) and 2-methoxycarbonyl-5-aminobenzofuran (36 mg, 0.18 mmol) in dry MeOH (0.5 ml) was refluxed for 2 days (100° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and subjected to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | CO | 100 | null | COC(=O)c1cc2cc(N)ccc2o1.Nc1cccc(Nc2nc(Cl)ncc2F)c1>CO>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(N)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-165cf36889044a42a70eee1919825547 | Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1.OCCBr>>OCCNc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.BrCCO>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)NCCO | [NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]4[c:22]([cH:23]3)[O:24][CH2:25][CH2:26][O:27]4)[n:28]2)[cH:29]1.Br[CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c... | Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1.OCCBr | OCCNc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | N2-(3-Aminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine and 2-bromoethanol were reacted together to give N4-(3,4-ethylenedioxyphenyl)-N2-[3-(hydroxyethylamino)phenyl]-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 15.44 min.; purity: 98.6%; MS (m/e): 398.05 (MH+).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HBr | null | null | null | Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1.OCCBr>>OCCNc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abba57d28a8c48089a9043a434bb1c7d | CCOC(=O)c1cnc(Cl)nc1NOCc1ccccc1.Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1NOCc1ccccc1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.C(C1=CC=CC=C1)ONC1=NC(=NC=C1C(=O)OCC)Cl.O1CCOC2=C1C=CC(=C2)N>>C(C1=CC=CC=C1)ONC1=NC(=NC=C1C(=O)OCC)NC1=CC2=C(C=C1)OCCO2 | Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:22]([NH:23][O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:21]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[O:17][CH2:18][CH2:19][O:20]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([c... | CCOC(=O)c1cnc(Cl)nc1NOCc1ccccc1.Nc1ccc2c(c1)OCCO2 | CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1NOCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CONc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, N4-benzyloxy-2-chloro-5-ethoxycarbonyl-4-pyrimidineamine and 1,4-benzodioxan-6-amine were reacted to yield N4-benzyloxy-5-ethoxycarbonyl-N2-(3,4-ethylenedioxyphenyl)-2,4-pyrimidinediamine. 1H NMR ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1cnc(Cl)nc1NOCc1ccccc1.Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1NOCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b7f45fdf5074d1f9d949025844eaa06 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(=O)O)cc1>>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 | NC1=CC=C(C(=O)O)C=C1.ClC1=NC=C(C(=N1)Cl)F>>C(=O)(O)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(=O)O)F | Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14](Cl)[n:15]1.[O:1]=[C:20]([OH:3])[c:19]1[cH:2][cH:6][c:7]([NH2:8])[cH:24][cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]3)[n:25]2)[cH:26][cH:27]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(=O)O)cc1 | O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | c1c7593995d253373f76f8a46498296703c24d6c383a23f9cb20785395565926 | c88b6dec908989f50e679dd543e66d3b17102134318371eb87c8c1c7ff491f32 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c;H0;D3;+0:12](-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[OH;D1;+0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c;H0;D3;+0:9]2:[c:1... | null | [] | 100 | CELSIUS | 24 | HOUR | A mixture of 4-Aminobenzoic acid (410 mg, 3 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) in methanol (10 mL) and water (1 mL) was stirred at 100° C. for 24 h to yield N2,N4-bis(4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine after methanol was removal. This residue was redissolved in DMF (10 mL) and to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 100 | 24 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(=O)O)cc1>O.CO>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b9e268d11cb48f4a1efac0b3e867430 | COC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OC)c3)n2)c1>>O=C(O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)O)c3)n2)c1 | COC(=O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)OC)F.[OH-].[Na+]>>C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([C:22](=[O:23])[O:24]C)[cH:25]3)[n:26]2)[cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][... | COC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OC)c3)n2)c1 | O=C(O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)O)c3)n2)c1 | null | null | O.C(C)(=O)OCC.C1CCOC1 | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 58.6 | [{"value": 58.0, "product": "C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N2,N4-bis(3-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine (100 mg, 0.25 mmol) and NaOH (140 mg, 3.5 mmol) in THF:H2O (5 mL, each) was stirred at room temperature overnight. The reaction mixture was diluted with water (60 mL) and ethyl acetate (60 mL). The aqueous layer was separated, acidified wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | O.C(C)(=O)OCC.C1CCOC1 | null | null | COC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OC)c3)n2)c1>O.C(C)(=O)OCC.C1CCOC1>O=C(O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-75b3748fad2c440bbfda5a21750e33c8 | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)cc3)n2)cc1>>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 | C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F.COC(=O)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(=O)OC)F.[OH-].[Na+]>>C(=O)(O)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(=O)O)F | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22]C)[cH:23][cH:24]3)[n:25]2)[cH:26][cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([C:20](=... | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)cc3)n2)cc1 | O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 59.7 | [{"value": 59.0, "product": "C(=O)(O)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(=O)O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "C(=O)(O)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(=O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(4-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine (100 mg, 0.25 mmol) and NaOH (200 mg, 5 mmol) gave N2,N4-bis(4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine (55 mg, 59%) as a white solid. 1H NMR (CD3... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)cc3)n2)cc1>>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5d55c2821a143a982b08bf405e3fcae | CCN=C=O.Nc1ccc(N)cc1>>CCNC(=O)Nc1ccc(N)cc1 | NC1=CC=C(C=C1)N.C(C)N=C=O.C([O-])([O-])=O.[K+].[K+]>>C(C)NC(=O)NC1=CC=C(N)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]1 | CCN=C=O.Nc1ccc(N)cc1 | CCNC(=O)Nc1ccc(N)cc1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 62 | [{"value": 62.0, "product": "C(C)NC(=O)NC1=CC=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "C(C)NC(=O)NC1=CC=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 1,4-diaminobenzene (4 g, 37 mmol), ethyl isocyanate (1 mL, 12.6 mmol) and potassium carbonate (8.72 g, 63 mmol) in THF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned in 1N HCl solution (80 mL) and ethyl acetate (80 mL). The aqueous layer was extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | C1CCOC1 | null | 8 | CCN=C=O.Nc1ccc(N)cc1>C1CCOC1>CCNC(=O)Nc1ccc(N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-318eb3db688b47298f4b6e6f63286912 | CCNC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCNC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)NCC)c3)n2)c1 | C(C)NC(=O)NC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)Cl)F>>C(C)NC(=O)NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NC(=O)NCC)F | [cH:1]1[c:2]([NH:3][C:4](=[O:5])[NH:28][CH2:29][CH3:30])[cH:31][c:20]([NH2:6])[cH:21][cH:7]1.Cl[c:13]1[n:14][cH:15][c:16]([F:17])[c:18](Cl)[n:32]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([NH:12][c:13]2[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]3[cH:21][cH:22][cH:23][c:24]([NH:25][C:2... | CCNC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl | CCNC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)NCC)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2212e2edf197989668b7395ad40e1bd22e58c8274f28f1648c7706fa3eea5675 | 79e66a9fdc830819ca1ede794ca41c79bc66afd81eff69c141e6dc29ce5968e2 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[C;D1;H3:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#7:13]-[c;H0;D3;+0:14]1:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18](-[NH2;D1;+0:19]):[cH;D2;+0:20]:1>>[C;D1;H3:8]-[C:9]-[NH;D2;+0:10]-[C:21](=[O;D1;H0:22])-[... | 66.3 | [{"value": 66.0, "product": "C(C)NC(=O)NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NC(=O)NCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "C(C)NC(=O)NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NC(=O)NCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis[4-(ethylaminocarbonylamino)phenyl]-5-fluoro-2,4-pyrimidinediamine, the reaction of 1,3-diaminobenzene (2 g, 18.5 mmol), ethyl isocyanate (0.5 mL, 6.3 mmol) and potassium carbonate (4.36 g, 31.5 mmol) gave 3-(ethylaminocarbonylamino)aniline (940 mg, 83%). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Urea.Primary amine | Urea.Urea.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CCNC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCNC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)NCC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1cb1f464b514912874358beb89722b2 | CO.Nc1ccc(C(=O)O)c(O)c1>>COC(=O)c1ccc(N)cc1O | NC1=CC(=C(C(=O)O)C=C1)O.CO>>OC=1C=C(N)C=CC1C(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[OH:12] | CO.Nc1ccc(C(=O)O)c(O)c1 | COC(=O)c1ccc(N)cc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 4-amino-2-hydroxybenzoic acid (1 g, 6.5 mmol) in MeOH (15 mL) and concentrated sulfonic acid (1 mL) was refluxed overnight. The reaction mixture was quenched with NaHCO3 aqueous solution (60 mL) and EtOAc (60 mL). The organic layer was separated, dried, evaporated to give 3-hydroxy-4-methoxycarbonylanilin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Nc1ccc(C(=O)O)c(O)c1>>COC(=O)c1ccc(N)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8044457b20634776897330f15b853cee | COC(=O)c1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.OC=1C=C(N)C=CC1C(=O)OC.ClC1=NC=C(C(=N1)Cl)F>>OC=1C=C(C=CC1C(=O)OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)OC)O)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:29][c:30]1[OH:31].Fc1cn[c:10](Cl)n[c:25]1Cl.c1cc(Nc2[c:13]([F:14])[cH:12][n:11][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:27]3)[n:28]2)c[c:24]([OH:23])c1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([F:1... | COC(=O)c1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O | null | null | null | Acylation | OtherReaction | 8c7afdae4f438416f0c519a7645fcad038f2fd161ea4b8f1b67b551d23cdc5ca | be93a118ade5b6169ff4b70426fe903330466be61c5fe0e675e6d6380660f4f5 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:n:c:c(-F):[c;H0;D3;+0:2](-Cl):n:1.[F;D1;H0:3]-[c;H0;D3;+0:4]1:[c:5]:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[#7:8]-[c:9]2:[c:10]:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[OH;D1;+0:14]):[cH;D2;+0:15]:2):[n;H0;D2;+0:16]:c:1-N-c1:c:c:c:[c;H0;D3;+0:17](-[OH;D1;+0:18]):c:1.[NH2;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[CH3;... | 41 | [{"value": 41.0, "product": "OC=1C=C(C=CC1C(=O)OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)OC)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 3-hydroxy-4-methoxycarbonylaniline (500 mg, 3 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave N2,N4-bis-[3-hydroxy-4-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine (105 mg, 41%). 1H NMR (DMS... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine | Aromatic halide.Ester.Aromatic alcohol.Secondary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HF | null | null | null | COC(=O)c1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29f45c3b82d74e4e8e026e61903c813a | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O>>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(O)c3)n2)cc1O | C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F.OC=1C=C(C=CC1C(=O)OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)OC)O)F.[OH-].[Na+]>>OC=1C=C(C=CC1C(=O)O)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)O)F | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22]C)[c:23]([OH:24])[cH:25]3)[n:26]2)[cH:27][c:28]1[OH:29]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][... | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O | O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(O)c3)n2)cc1O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 78.1 | [{"value": 77.0, "product": "OC=1C=C(C=CC1C(=O)O)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "OC=1C=C(C=CC1C(=O)O)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of N2,N4-bis[3-hydroxy-4-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine (70 mg, 0.16 mmol) and NaOH (100 mg, 2.5 mmol) gave N2,N4-bis(3-hydroxy-4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine (50... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(O)c3)n2)cc1O>>O=C(O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(O)c3)n2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35d893c636d6464493fa96231bc7782b | CI.COc1cc([N+](=O)[O-])ccc1C(=O)O>>COC(=O)c1ccc([N+](=O)[O-])cc1OC | COC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].IC>>COC1=C(C(=O)OC)C=CC(=C1)[N+](=O)[O-] | I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[O:14][CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[O:14][CH3:15] | CI.COc1cc([N+](=O)[O-])ccc1C(=O)O | COC(=O)c1ccc([N+](=O)[O-])cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 77.7 | [{"value": 77.0, "product": "COC1=C(C(=O)OC)C=CC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "COC1=C(C(=O)OC)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis[4-(2-methyl-1,2,3,4-tetrazol-5-yl)methyleneoxyphenyl]-5-fluoro-2,4-pyrimidinediamine, 2-methoxy-4-nitrobenzoic acid (1 g, 5 mmol), potassium carbonate (1.4 g, 10 mmol) and iodomethane (0.47 mL, 7.5 mmol) gave methyl 2-methoxy-4-nitrobenzoate (820 mg, 77%) as a white... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | null | null | null | CI.COc1cc([N+](=O)[O-])ccc1C(=O)O>>COC(=O)c1ccc([N+](=O)[O-])cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62d99dab619c4632ad642cb3c4d62e4f | COC(=O)c1ccc([N+](=O)[O-])cc1OC>>COC(=O)c1ccc(N)cc1OC | COC1=C(C(=O)OC)C=CC(=C1)[N+](=O)[O-].[O-]S(=O)(=O)[O-].[Na+].[Na+]>>NC1=CC(=C(C(=O)OC)C=C1)OC | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([O:12][CH3:13])[cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[O:12][CH3:13] | COC(=O)c1ccc([N+](=O)[O-])cc1OC | COC(=O)c1ccc(N)cc1OC | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.3 | [{"value": 100.3, "product": "NC1=CC(=C(C(=O)OC)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The hydrogenation of methyl 2-methoxy-4-nitrobenzoate (700 mg, 3.3 mmol) in methanol (10 mL) catalyzed by 5% Pd—C (100 mg) and Na2SO4 (100 mg) at 50 psi for 1 h gave methyl 4-amino-2-methoxybenzoate (600 mg, quant.) as a white solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | COC(=O)c1ccc([N+](=O)[O-])cc1OC>[Pd].CO>COC(=O)c1ccc(N)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12d5a470745841e99e1b8403260039aa | CI.O=C(O)c1cc([N+](=O)[O-])ccc1O>>COC(=O)c1cc([N+](=O)[O-])ccc1O | FC=1C(=NC(=NC1)N)N.OC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].IC>>OC1=C(C(=O)OC)C=C(C=C1)[N+](=O)[O-] | I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[OH:14] | CI.O=C(O)c1cc([N+](=O)[O-])ccc1O | COC(=O)c1cc([N+](=O)[O-])ccc1O | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 77 | [{"value": 77.0, "product": "OC1=C(C(=O)OC)C=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-methoxy-4-methoxycarbonyl)phenyl)-5-fluoro-2,4-pyrimidinediamine, 2-hydroxy-5-nitrobenzoic acid (1 g, 5.5 mmol), potassium carbonate (3 g, 22 mmol) and iodomethane (1 mL, 16 mmol) gave methyl 2-hydroxy-5-nitrobenzoate (880 mg, 77%).
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | null | null | null | CI.O=C(O)c1cc([N+](=O)[O-])ccc1O>>COC(=O)c1cc([N+](=O)[O-])ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29c3e4e1a52e4fed88b383eb0c4c4788 | CO.COC(=O)c1cc([N+](=O)[O-])ccc1O>>COC(=O)c1cc(N)ccc1OC | OC1=C(C(=O)OC)C=C(C=C1)[N+](=O)[O-].[O-]S(=O)(=O)[O-].[Na+].[Na+].CO>>NC=1C=CC(=C(C(=O)OC)C1)OC | O[CH3:13].O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([OH:12])[cH:10][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[O:12][CH3:13] | CO.COC(=O)c1cc([N+](=O)[O-])ccc1O | COC(=O)c1cc(N)ccc1OC | null | [Pd] | null | Functional Group Interconversion | OtherReaction | 2e9daf3a7d652c50c3391208f0c5b6bc49dfb6e02fd0ac4cf2d81f837ac1b2db | 62fef7d6d16eff766f41839348c4f709c9a621e22a5cd1cb4d721c078a142f8a | c1ccccc1 | O-[CH3;D1;+0:1].O=[N+;H0;D3:2](-[O-])-[c:3]1:[c:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9](-[OH;D1;+0:10]):[c:11]:[c:12]:1>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[c:4]:[c:3](-[NH2;D1;+0:2]):[c:12]:[c:11]:[c:9]:1-[O;H0;D2;+0:10]-[CH3;D1;+0:1] | null | [] | null | null | null | null | The hydrogenation of methyl 2-hydroxy-5-nitrobenzoate (700 mg, 3.3 mmol) using 10% Pd—C (100 mg) and Na2SO4 (100 mg) in MeOH at 50 psi gave methyl 5-amino-2-methoxybenzoate (600 mg).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Methanol | Ether.Primary amine | null | null | c1ccccc1 | Other | [Pd] | null | null | CO.COC(=O)c1cc([N+](=O)[O-])ccc1O>[Pd]>COC(=O)c1cc(N)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-525b5e389f8644eebcc0e15db1ee0a9d | COC(=O)c1cc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)OC)c3)n2)ccc1OC>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)O)c3)n2)cc1C(=O)O | C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F.COC1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)OC)F)C(=O)OC.[OH-].[Na+]>>C(=O)(O)C=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)O)F | C[O:24][C:22]([c:21]1[c:18]([O:19][CH3:20])[cH:17][cH:16][c:15]([NH:14][c:13]2[c:11]([F:12])[cH:10][n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([C:29](=[O:30])[O:31]C)[cH:27]3)[n:26]2)[cH:25]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16]... | COC(=O)c1cc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)OC)c3)n2)ccc1OC | COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)O)c3)n2)cc1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 103.8 | [{"value": 103.8, "product": "C(=O)(O)C=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis[4-methoxy-3-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine (80 mg, 0.18 mmol) and NaOH (200 mg, 5 mmol) gave N2,N4-bis(3-carboxy-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine (80 mg). 1H NMR (DMSO... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)OC)c3)n2)ccc1OC>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(C(=O)O)c3)n2)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-360161db925c49758b5c263e89087897 | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(OC)c3)n2)cc1OC>>COc1cc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(OC)c3)n2)ccc1C(=O)O | C(=O)(O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)O)F.COC=1C=C(C=CC1C(=O)OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)OC)OC)F.[OH-].[Na+]>>C(=O)(O)C1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)OC)F)OC | C[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([NH:13][c:12]2[c:10]([F:11])[cH:9][n:8][c:7]([NH:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:28]([C:29](=[O:30])[O:31]C)[cH:27][cH:26]3)[n:25]2)[cH:24][c:21]1[O:22][CH3:23])=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][c... | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(OC)c3)n2)cc1OC | COc1cc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(OC)c3)n2)ccc1C(=O)O | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 70 | [{"value": 64.0, "product": "C(=O)(O)C1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)OC)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "C(=O)(O)C1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)O)OC)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-methoxy-4-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine (30 mg, 0.06 mmol) and NaOH (200 mg, 5 mmol) gave N2,N4-bis(4-carboxy-3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine (18 mg, 64%) as a white... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1ccc(Nc2ncc(F)c(Nc3ccc(C(=O)OC)c(OC)c3)n2)cc1OC>>COc1cc(Nc2ncc(F)c(Nc3ccc(C(=O)O)c(OC)c3)n2)ccc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-784fc067c6394e379ba0fb377320fb95 | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1 | C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.Cl.CN>>C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]4)[n:28]3)[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14... | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1 | CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of N4-(4-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine with methylamine hydrochloride gave N4-(4-tert-butylphenyl)-5-fluoro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c660b15c6117450d9951cd5e749044a6 | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.Cl.CN>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27]4)[n:28]3)[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14... | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, N4-(3-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidinediamine and methylamine hydrochloride were reacted to give N4-(3-tert-butylphenyl)-5-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-220f9f11bc91425489578e98c01b8766 | CC(C)(N)CO.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>CC(C)(CO)NC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)O.NC(CO)(C)C>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)NC(CO)(C)C)C1)NC1=CC(=CC=C1)O | [CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[NH2:6].CO[C:7](=[O:8])[c:9]1[cH:10][c:11]2[cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][c:18]([F:19])[c:20]([NH:21][c:22]4[cH:23][cH:24][cH:25][c:26]([OH:27])[cH:28]4)[n:29]3)[cH:30][cH:31][c:32]2[o:33]1>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[NH:6][C:7](=[O:8])[c:9]1[cH:10][c:11]2[cH:12]... | CC(C)(N)CO.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | CC(C)(CO)NC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine and 2-amino-2-methylpropanol were reacted to yield 5-fluoro-N2-[2-(2-hydroxy-1... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CC(C)(N)CO.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>CC(C)(CO)NC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-321ab2568d6c4265a8eb88ca61f1b16a | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)O.Cl.CN>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)NC)C1)NC1=CC(=CC=C1)O | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]4)[n:25]3)[cH:26][cH:27][c:28]2[o:29]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:1... | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine with methylamine hydrochloride gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a681c986d31343faad7647f5660da81e | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1.NCCO>>O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)O.OCCN>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)NCCO)C1)NC1=CC(=CC=C1)O | CO[C:2](=[O:1])[c:7]1[cH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]4[cH:21][cH:22][cH:23][c:24]([OH:25])[cH:26]4)[n:27]3)[cH:28][cH:29][c:30]2[o:31]1.[NH2:3][CH2:4][CH2:5][OH:6]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[c:7]1[cH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1.NCCO | O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine with 2-hydroxyethylamine gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2-(N-2-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1.NCCO>>O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80093b97ea0b4e36898f2eecd6f35390 | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.Cl.CN>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)NC)C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]5[c:22]([cH:23]4)[O:24][CH2:25][CH2:26][O:27]5)[n:28]3)[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:... | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3occc3c2)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine and methylamine hydrochloride gave N4-(3,4-ethylenedioxyphenyl)... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CN.COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1>>CNC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00103d1a183b43d5bcf17e9d1978da58 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCCO>>O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.OCCN>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)NCCO)C1 | CO[C:2](=[O:1])[c:7]1[cH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]4[cH:21][cH:22][c:23]5[c:24]([cH:25]4)[O:26][CH2:27][CH2:28][O:29]5)[n:30]3)[cH:31][cH:32][c:33]2[o:34]1.[NH2:3][CH2:4][CH2:5][OH:6]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[c:7]1[cH:8][c:9]2[cH:10][c:11]([NH:12]... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCCO | O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3occc3c2)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine with 2-hydroxyethylamine yielded N4-(3,4-ethylenedioxyphenyl)-5... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCCO>>O=C(NCCO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38fe53899eb14c37ae7eaa4046e1c5d1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCC(O)CO>>O=C(NCC(O)CO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.OC(CN)CO>>OC(CNC(=O)C=1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC2=CC1=C(C=C2)OCCO1)F)CO | CO[C:2](=[O:1])[c:9]1[cH:10][c:11]2[cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][c:18]([F:19])[c:20]([NH:21][c:22]4[cH:23][cH:24][c:25]5[c:26]([cH:27]4)[O:28][CH2:29][CH2:30][O:31]5)[n:32]3)[cH:33][cH:34][c:35]2[o:36]1.[NH2:3][CH2:4][CH:5]([OH:6])[CH2:7][OH:8]>>[O:1]=[C:2]([NH:3][CH2:4][CH:5]([OH:6])[CH2:7][OH:8])[c:9]1[cH... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCC(O)CO | O=C(NCC(O)CO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3occc3c2)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine and 2,3-dihydroxypropylamine gave N2-[2-(N-2,3-dihydroxypropylamino)carbony... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1.NCC(O)CO>>O=C(NCC(O)CO)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02ba7352cf8f47929773c1a8a6b88a11 | CN.COC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1>>CNC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)F.Cl.CN>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC=1C=CC2=C(C=C(O2)C(=O)NC)C1)F | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]5[c:19]([cH:20]4)[O:21][CH2:22][CH2:23][O:24]5)[n:25][cH:26][c:27]3[F:28])[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH:14][c:15... | CN.COC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1 | CNC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cc(Nc2ccc3occc3c2)nc(Nc2ccc3c(c2)OCCO3)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of N2-(3,4-ethylenedioxyphenyl)-N4-(2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine with methylamine hydrochloride gave N2-(3,4-ethylenedioxyphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CN.COC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1>>CNC(=O)c1cc2cc(Nc3nc(Nc4ccc5c(c4)OCCO5)ncc3F)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c990984cd194f77b54febb648cc980a | O=C1COc2ccc(Nc3ncc(F)c(Nc4cccc([N+](=O)[O-])c4)n3)cc2N1>>Nc1cccc(Nc2nc(Nc3ccc4c(c3)N=CCO4)ncc2F)c1 | [N+](=O)([O-])C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(NC(CO2)=O)C1.O.Cl>>NC=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(N=CCO2)C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[NH:18][C:19](=O)[CH2:20][O:21]4)[n:22][cH:23][c:24]2[F:25])[cH:26]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[N:18]=[CH:19][CH2:... | O=C1COc2ccc(Nc3ncc(F)c(Nc4cccc([N+](=O)[O-])c4)n3)cc2N1 | Nc1cccc(Nc2nc(Nc3ccc4c(c3)N=CCO4)ncc2F)c1 | null | [Pd] | CCO | Functional Group Interconversion | OtherReaction | 9d73135e6c9c94bc1aa4cc571f568b84cdb4a3c2c34afb1a5325150b63890143 | 654efe6986f123b14b99c323ad5333593cae5ff0b12fbfaf80335c309582720b | C1=Nc2cc(Nc3nccc(Nc4ccccc4)n3)ccc2OC1 | O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[c:4]:[c:5](:[c:6])-[NH;D2;+0:7]-1.O=[N+;H0;D3:8](-[O-])-[c:9](:[c:10]):[c:11]>>[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11].[c:6]:[c:5]1:[c:4]-[#8:3]-[C:2]-[CH;D2;+0:1]=[N;H0;D2;+0:7]-1 | 21.2 | [{"value": 21.2, "product": "NC=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(N=CCO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N4-(3-Nitrophenyl)-N2-[(2H) 1,4-benzoxazin-3(4H)-one-6-yl]-5-fluoro-2,4-pyrimidinediamine (940 mg, 2.5 mmol) and Pd/C10% (300 mg, 50% water content) were suspended in EtOH (7 mL) and 10% aqueous HCl (5 mL) and hydrogenated in a Parr apparatus for 3 hours (22° C., 60 psi). The suspension was filtered over celite and neu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amide | Substituted imine.Primary amine | c1ccc2c(c1)NCCO2 | C1=Nc2ccccc2OC1 | c1ccccc1.c1cncnc1.C1=Nc2ccccc2OC1 | Other | [Pd].CCO | null | null | O=C1COc2ccc(Nc3ncc(F)c(Nc4cccc([N+](=O)[O-])c4)n3)cc2N1>[Pd].CCO>Nc1cccc(Nc2nc(Nc3ccc4c(c3)N=CCO4)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8c29f8a8d554ce8867c30cc6a2a134e | Cl>>Cl | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)OCCNC.Cl>>Cl.C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)OCCNC | [ClH:31]>>[ClH:31] | Cl | Cl | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[2-(N-piperazino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine Hydrogen Chloride Salt, the reaction of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-[2-(N-methylamino)ethyloxy]phenyl]-2,4-pyrimidinediamine with hydrogen chloride (4M, dioxane) ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | Cl>>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0dae7809e7884c6cb3882007886d115a | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1>>OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | C1ON2C(=NC=C(C2(N)OC1)F)NC=1C=CC2=C(C=C(O2)CO)C1.FC=1C(=NC(=NC1)NC=1C=C2C=C(NC2=CC1)C(=O)OC)NC1=CC(=CC=C1)O.CC(C)C[AlH]CC(C)C>>FC=1C(=NC(=NC1)NC=1C=C2C=C(NC2=CC1)CO)NC1=CC(=CC=C1)O | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]4)[n:23]3)[cH:24][cH:25][c:26]2[nH:27]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20](... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ccnc(Nc3ccc4[nH]ccc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine, 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2-(methoxycarbonyl)-(1H)-indol-5-yl]-2,4-pyrimidinediamine was reduced with DIBALH to yield 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2-(hydroxymethyl)-(1H)-in... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1>>OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-969db695386e42e2a176b4e9dda6a444 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1>>CC(C)Oc1ccc(Nc2nc(Nc3ccc4oc(CO)cc4c3)ncc2F)cc1 | C1ON2C(=NC=C(C2(N)OC1)F)NC=1C=CC2=C(C=C(O2)CO)C1.FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC=C(C=C1)OC(C)C.CC(C)C[AlH]CC(C)C>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)CO)C1)NC1=CC=C(C=C1)OC(C)C | CO[C:20]([c:19]1[o:18][c:17]2[cH:16][cH:15][c:14]([NH:13][c:12]3[n:11][c:10]([NH:9][c:8]4[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:30][cH:29]4)[c:27]([F:28])[cH:26][n:25]3)[cH:24][c:23]2[cH:22]1)=[O:21]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1 | CC(C)Oc1ccc(Nc2nc(Nc3ccc4oc(CO)cc4c3)ncc2F)cc1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine, 5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine was reduced with DIBALH to yield 5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(4-isopro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cncnc1.c1ccc2occc2c1 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1>>CC(C)Oc1ccc(Nc2nc(Nc3ccc4oc(CO)cc4c3)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8a4ed5e8726447dbd9e14fba321c239 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | C1ON2C(=NC=C(C2(N)OC1)F)NC=1C=CC2=C(C=C(O2)CO)C1.FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC(=CC=C1)O.CC(C)C[AlH]CC(C)C>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)CO)C1)NC1=CC(=CC=C1)O | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]4)[n:23]3)[cH:24][cH:25][c:26]2[o:27]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20]([... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine, 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2-(methoxycarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine was reduced with DIBALH to yield 5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(3-hydroxy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1>>OCc1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7b68239decc4401b9f8acb69515500b | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1>>CC(C)(C)c1cccc(Nc2nc(Nc3ccc4c(c3)CC(=CO)O4)ncc2F)c1 | C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.CC(C)C[AlH]CC(C)C>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)=CO)C1 | C[O:24][C:23](=O)[c:22]1[cH:21][c:19]2[c:18]([cH:17][cH:16][c:15]([NH:14][c:13]3[n:12][c:11]([NH:10][c:9]4[cH:8][cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:30]4)[c:28]([F:29])[cH:27][n:26]3)[cH:20]2)[o:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:15]3[c... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1 | CC(C)(C)c1cccc(Nc2nc(Nc3ccc4c(c3)CC(=CO)O4)ncc2F)c1 | null | null | null | Miscellaneous | OtherReaction | cd6bec24aad33c97e64b84bc4bc155bee9d2c3df71dea96bdb707f7ded572b2b | 3fcf2578812d33862f379bcae1621f7606190651cdb834d7f1887646ff868e5f | [CH]=C1Cc2cc(Nc3nccc(Nc4ccccc4)n3)ccc2O1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:8]):[o;H0;D2;+0:9]:1>>[OH;D1;+0:1]-[CH;D2;+0:2]=[C;H0;D3;+0:3]1-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[3-[2-(N-morpholino)ethyleneoxy]phenyl]-2,4-pyrimidinediamine, N4-(3-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofur-5-yl)-2,4-pyrimidinediamine reacted with DIBALH to give N4-(3-tert-butylphenyl)-5-fluoro-N2-[2-(hydroxymethylene)ben... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ether.Enol | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1cncnc1.c1ccc2c(c1)CCO2 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(C(C)(C)C)c4)n3)ccc2o1>>CC(C)(C)c1cccc(Nc2nc(Nc3ccc4c(c3)CC(=CO)O4)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5357eb2572384861a7f2dafc1a7b37c4 | CCOC(=O)C(C)(C)c1ccc(NC2=NC(Cl)(Nc3ccc4c(c3)OCCO4)NC=C2F)cc1>>CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | ClC1(NC=C(C(=N1)NC1=CC=C(C=C1)C(C)(C)C(=O)OCC)F)NC1=CC2=C(C=C1)OCCO2.CC(C)C[AlH]CC(C)C>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(CO)(C)C)F | CCO[C:4]([C:2]([CH3:1])([CH3:3])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11]2=[N:12][C:13](Cl)([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][CH2:23][O:24]4)[NH:25][CH:26]=[C:27]2[F:28])[cH:29][cH:30]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:1... | CCOC(=O)C(C)(C)c1ccc(NC2=NC(Cl)(Nc3ccc4c(c3)OCCO4)NC=C2F)cc1 | CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 171c84771f9a9e3771852a3ddd4b0f049240be598b389e492b95c7c697382197 | e2207bbc7c5b098edceef9a78c68a5207130be04e3178c66a667dfd7098402e9 | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6].Cl-[C;H0;D4;+0:7]1(-[#7:8]-[c:9])-[N;H0;D2;+0:10]=[C;H0;D3;+0:11](-[#7:12]-[c:13])-[C;H0;D3;+0:14](-[F;D1;H0:15])=[CH;D2;+0:16]-[NH;D2;+0:17]-1>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[c:6])-[CH2;D2;+0:1]-[OH;D1;+0:2].[F;D1;H0:15]-[c;H0;D3;+0:14]1:... | null | [] | null | null | 30 | MINUTE | 2-Chloro-5-fluoro-N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-N2-(3,4-ethylenedioxyphenyl)-2,4-pyrimidinediamine was reduced with 10 eq. DIBALH (1.0 M in toluene) at 0° C. in dichloromethane. Reaction was quenched with methanol, diluted with ethylacetate followed by the addition of aqueous Rochelle's salt solution, s... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Tertiary halide.Alkenyl halide.Ester | Aromatic halide.Primary alcohol | C1=CNCN=C1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | ClCCl | null | 0.5 | CCOC(=O)C(C)(C)c1ccc(NC2=NC(Cl)(Nc3ccc4c(c3)OCCO4)NC=C2F)cc1>ClCCl>CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff605ccc39d540e892fcbe4a89ef5c20 | CCOC(=O)C(C)(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1>>CC(C)(CO)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | C(C)OC(=O)C(C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F)(C)C.CC(C)C[AlH]CC(C)C>>FC=1C(=NC(=NC1)NC1=CC=C(C=C1)C(CO)(C)C)NC1=CC(=CC=C1)O | CCO[C:4]([C:2]([CH3:1])([CH3:3])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]3)[n:25]2)[cH:26][cH:27]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH... | CCOC(=O)C(C)(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | CC(C)(CO)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[c:6])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | In like manner to the preparation of N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]-2,4-pyrimidinediamine, N2-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine was reduced with DIBALH to provide 5-fluoro-N2-[4-(2-hydroxy-1,1-dimethylethyl)ph... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)C(C)(C)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1>>CC(C)(CO)c1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-064f0623906b4055997fa865a8736f6f | CC(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)CC(C(=O)O)O4)ncc2F)cc1.[OH-]>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)O)C1.[Li+].[OH-]>>C(=O)(O)C=1OC2=C(C1)C=C(C=C2)NC2=NC=C(C(=N2)NC2=CC(=CC=C2)O)F | CC(C)(C)[c:20]1[cH:19][cH:18][c:17]([NH:16][c:15]2[c:13]([F:14])[cH:12][n:11][c:10]([NH:9][c:8]3[cH:7][c:6]4[c:27]([cH:26][cH:25]3)[O:28][CH:4]([C:2](=[O:1])[OH:3])[CH2:5]4)[n:24]2)[cH:23][cH:21]1.[OH-:22]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]4[cH... | CC(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)CC(C(=O)O)O4)ncc2F)cc1.[OH-] | O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b9581145d81156be2a1a9fc422ba92475bc5ce5bb599bfde07b37482f8a26f8e | 7f3b1b26d2218a50076273b3df13eaa65acef18a61d420fcdb62b39284d890a2 | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-C(-C)(-C)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:14](:[c:15])-[O;H0;D2;+0:16]-1.[OH-;D0:17]>>[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14](:[c:15]):[o;H0;D2;+0:16]:1.[OH;D1;+0:17]-[... | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(carboxy)benzofuran-5-yl]-2,4-pyrimidinediamine, 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-4-pyrimidinediamine upon LiOH treatment gave N2-(2-carboxybenzofuran-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-p... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccc2occc2c1.c1ccccc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | Other | null | null | null | CC(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)CC(C(=O)O)O4)ncc2F)cc1.[OH-]>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d5a338c3b2f4c7cbe8683f9f74d1b20 | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)O)C1.C(C)OC(=O)C=1NC2=CC=C(C=C2C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.[Li+].[OH-]>>C(=O)(O)C=1NC2=CC=C(C=C2C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]4[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:23]4)[n:24]3)[cH:25][cH:26][c:27]2[nH:28]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]4[cH:18][cH:19][... | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccnc(Nc3ccc4[nH]ccc4c3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(carboxy)benzofuran-5-yl]-2,4-pyrimidinediamine, N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine upon LiOH treatment gave N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccccc1 | Other | null | null | null | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4cccc(O)c4)n3)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c631e3c8605048cab77f2a6c0bbc8e2d | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1>>CC(C)(C)c1ccc(Nc2nc(Nc3ccc4oc(C(=O)O)cc4c3)ncc2F)cc1 | C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)O)C1.[Li+].[OH-].C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1>>C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)O)C1 | C[O:22][C:20]([c:19]1[o:18][c:17]2[cH:16][cH:15][c:14]([NH:13][c:12]3[n:11][c:10]([NH:9][c:8]4[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]4)[c:28]([F:29])[cH:27][n:26]3)[cH:25][c:24]2[cH:23]1)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1 | CC(C)(C)c1ccc(Nc2nc(Nc3ccc4oc(C(=O)O)cc4c3)ncc2F)cc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(carboxy)benzofuran-5-yl]-2,4-pyrimidinediamine, LiOH treatment with N4-(4-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine gave N4-(4-tert-butylphenyl)-N2-(2-carboxybenzofuran-5-yl)-5-fluo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccc2occc2c1 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(C(C)(C)C)cc4)n3)ccc2o1>>CC(C)(C)c1ccc(Nc2nc(Nc3ccc4oc(C(=O)O)cc4c3)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7caf71b50cd443489ab5c07435af38b | CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>O=C(O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | C(C)OC(=O)C=NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.[Li+].[OH-].Cl>>C(=O)(O)C=NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | CC[O:3][C:2](=[O:1])[CH:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]4[c:23]([cH:24]3)[O:25][CH2:26][CH2:27][O:28]4)[n:29]2)[cH:30]1>>[O:1]=[C:2]([OH:3])[CH:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17](... | CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | O=C(O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[#7:5]>>[#7:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | The reaction of N2-(3-ethoxycarbonylmethyleneaminophenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine (0.1 g) and LiOH (10 equivalents) in MeOH:water (1:1, v/v) for 1 h at room temperature followed by treatment with aqueous HCl gave the solid. The resulting solid was filtered, washed with water and drie... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | Other | CO.O | null | null | CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>CO.O>O=C(O)C=Nc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b05ac673cb2c4894b01511ce3d0153fd | NCC(O)CO.O=C(O)C=Nc1ccccc1Nc1ncc(F)c(Nc2cccc(NCCO)c2)n1>>O=C(C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(NCCO)c3)n2)c1)NCC(O)CO | C(=O)(O)C=NC1=C(C=CC=C1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NCCO)F.NCC(CO)O>>OC(CNC(=O)C=NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NCCO)F)CO | [NH2:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35].O[C:2](=[O:1])[CH:3]=[N:4][c:5]1[cH:6][cH:7][cH:8][cH:29][c:9]1[NH:10][c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][c:22]([NH:23][CH2:24][CH2:25][OH:26])[cH:27]2)[n:28]1>>[O:1]=[C:2]([CH:3]=[N:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n... | NCC(O)CO.O=C(O)C=Nc1ccccc1Nc1ncc(F)c(Nc2cccc(NCCO)c2)n1 | O=C(C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(NCCO)c3)n2)c1)NCC(O)CO | null | null | null | Acylation | OtherReaction | cdc5a4b7bc8255d118c9bad2f06b1bf2850c05ad4e9688742b010a00bb74d5a8 | 1d370761a42c7e3d99dd332f8ef260e74660ebbea928762930430424311dbd3c | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[#7:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10]:1-[#7:11]-[c:12](:[#7;a:13]):[#7;a:14].[C:15]-[C:16]-[NH2;D1;+0:17]>>[#7;a:13]:[c:12](-[#7:11]-[c;H0;D3;+0:10]1:[cH;D2;+0:9]:[c;H0;D3;+0:5](-[#7:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:17]-[C:16]-[C... | null | [] | null | null | null | null | In like manner to the preparation of N4-[3-(2-hydroxyethylamino)phenyl]-N2-[3-[N-(2-hydroxyethylamino)]carbonylmethyleneaminophenyl]-5-fluoro-2,4-pyrimidinediamine, N2-(carboxymethyleneaminophenyl)-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine and 1-amino-2,3-propanediol were reacted to give N2-[3-[... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Substituted imine.Primary amine | Substituted imine.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | null | null | NCC(O)CO.O=C(O)C=Nc1ccccc1Nc1ncc(F)c(Nc2cccc(NCCO)c2)n1>>O=C(C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(NCCO)c3)n2)c1)NCC(O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0496633e234424196d7c613e47dfae5 | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)Cl)C(=O)OCC.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)C(=O)OCC | Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:22](Cl)[n:21]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[O:17][CH2:18][CH2:19][O:20]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[O:17][CH2:18][CH2:19][O:20]3)[n:21][c:22]1[NH:23][c:24... | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2 | CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 65aaf594a712f046e6a2a337c3dd02a9d692b9a78bf376c52cff916aa1ca0119 | 3aed760cb40507213c6f22bd77e177ef5f0f58739db0aa6c23cf287116ceff9a | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c;H0;D3;+0:1]:1-[#7:15]-[c:16] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis[N-(L)-tyrosine methyl ester]-5-ethoxycarbonylpyrimidine, the reaction of 2,4-dichloro-5-ethoxycarbonylpyrimidine with 3,4-ethylenedioxyaniline gave N2,N4-bis(3,4-ethylenedioxyphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.01 (s, 1H), 9.65 (bs, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | null | null | null | null | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>>CCOC(=O)c1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f3c04230baf46e684aeeb991355e437 | CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1[N+](=O)[O-]>>CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N | C(C)OC(=O)C1=C(C(=NC(=N1)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)O)[N+](=O)[O-]>>NC=1C(=NC(=NC1C(=O)OCC)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)O | O=[N+:28]([O-])[c:27]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]2)[n:17][c:18]1[NH:19][c:20]1[cH:21][cH:22][cH:23][c:24]([OH:25])[cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]2)[n:17][c:1... | CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1[N+](=O)[O-] | CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C:9](-[#8:10])=[O;D1;H0:11]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[C:9](-[#8:10])=[O;D1;H0:11]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | null | null | A suspension of 6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-5-nitro-2,4-pyrimidinediamine and 10% Pd/C (10% by weight) in ethanol was prepared and reacted in a Parr bottle under hydrogen gas (20 PSI) for 1 h. The reaction mixture was filtered through Celite. Purification by column chromatography gave 5-amino-6-ethoxyca... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1[N+](=O)[O-]>[Pd].C(C)O>CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ded7b00dc9c4440a8b50c9feb2567a9f | CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1[N+](=O)[O-].CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N>>CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1N | NC=1C(=NC(=NC1C(=O)OCC)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)O.C(C)OC(=O)C1=C(C(=NC(=N1)NC1=CC2=C(C=C1)OCCO2)NC2=CC1=C(C=C2)OCCO1)[N+](=O)[O-].[H][H]>>NC=1C(=NC(=NC1C(=O)OCC)NC1=CC2=C(C=C1)OCCO2)NC2=CC1=C(C=C2)OCCO1 | CCOC(=O)c1nc(Nc2ccc3c(c2)[O:16][CH2:17][CH2:18][O:19]3)nc(Nc2ccc3c(c2)[O:29][CH2:30][CH2:31][O:32]3)c1[N+](=O)[O-].O[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][c:8]2[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33]([NH2:34])[c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][c:27](O)[cH:28]3)[n:20]2)[cH:15]1>>[CH3:1][CH2:2][O:3]... | CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1[N+](=O)[O-].CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N | CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1N | null | [Pd] | null | Functional Group Interconversion | OtherReaction | 1993b47cdf12ff256d0f1de58936f2561059587bdb070ef42a2d952fbf6c6188 | 7416b7aaab159a177ef3b43604d8c23072e98c651e594140de99a4b079b3ac86 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)n1 | C-C-O-C(=O)-c1:n:c(-N-c2:c:c:c3:c(:c:2)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-3):n:c(-N-c2:c:c:c3:c(:c:2)-[O;H0;D2;+0:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-3):c:1-[N+](=O)-[O-].O-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1.O-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18]:[c:19]:[cH;D2;+0:20]:1>>[C:2]1-[C:3]-[O;H0;D2... | null | [] | null | null | null | null | In a manner similar to the preparation of 5-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine, 6-ethoxycarbonyl-N2,N4-bis(3,4-ethylenedioxyphenyl)-5-nitro-2,4-pyrimidinediamine, hydrogen, and 10% Pd/C were reacted to yield 5-amino-6-ethoxycarbonyl-N2,N4-bis(3,4-ethylenedioxyphenyl)-2,4-pyrimidined... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Ether.Ether.Nitro group.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | Ether.Ether.Ether.Ether | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2.c1ccccc1.c1ccccc1 | c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HO- | [Pd] | null | null | CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1[N+](=O)[O-].CCOC(=O)c1nc(Nc2cccc(O)c2)nc(Nc2cccc(O)c2)c1N>[Pd]>CCOC(=O)c1nc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb31f21620034fe2a52ae93fef2aae6d | CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1>>CCOC(=O)CNc1nc(NCC(=O)OCC)c(N)c(C(=O)OCC)n1 | NC=1C(=NC(=NC1C(=O)OCC)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)O.C(C)OC(=O)C1=C(C(=NC(=N1)NCC(=O)OCC)NCC(=O)OCC)[N+](=O)[O-].[H][H]>>NC=1C(=NC(=NC1C(=O)OCC)NCC(=O)OCC)NCC(=O)OCC | O=[N+:19]([O-])[c:18]1[c:10]([NH:11][CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17])[n:9][c:8]([NH:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:26][c:20]1[C:21](=[O:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[n:9][c:10]([NH:11][CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17])[c:18]([NH2:1... | CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1 | CCOC(=O)CNc1nc(NCC(=O)OCC)c(N)c(C(=O)OCC)n1 | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cncnc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C:9](-[#8:10])=[O;D1;H0:11]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[C:9](-[#8:10])=[O;D1;H0:11]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | null | null | In a manner similar to the preparation of 5-amino-6-ethoxycarbonyl-N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine, 6-ethoxycarbonyl-N2,N4-bis(ethoxycarbonylmethyl)-5-nitro-2,4-pyrimidinediamine, hydrogen, and 10% Pd/C were reacted to yield 5-amino-N2,N4-bis(ethoxycarbonylmethyl)-6-ethoxycarbonyl-2,4-pyrimidinediamine... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1 | Other | [Pd] | null | null | CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1>[Pd]>CCOC(=O)CNc1nc(NCC(=O)OCC)c(N)c(C(=O)OCC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4282689ce60448c0ad5f18f0965294a0 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccnc1>>Fc1cnc(Nc2cccnc2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC=1C=NC=CC1.CC(C)([O-])C.[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C(C)(C)N(C(C)C)CC>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=NC=CC1 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:13]1.[NH2:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13][c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccnc1 | Fc1cnc(Nc2cccnc2)nc1Nc1ccc2c(c1)OCCO2 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[c:9]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:8] | 16.2 | [{"value": 14.0, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.2, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 24 | HOUR | A mixture of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine (280 mg, 1 mmol), 3-aminopyridine (113 mg, 1.2 mmol), sodium t-butoxide (134 mg, 1.4 mmol), binap (38 mg, 0.06 mmol), and palladium(II)acetate (14 mg, 0.06 mmol) in 9 mL of toluene was purged with N2 (3 cycles of alternating N2 and vacuum). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.c1ccc2c(c1)OCCO2 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | 80 | 24 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccnc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>Fc1cnc(Nc2cccnc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dcfab6b481a64fd389632694611ebcf3 | CCCCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCCCCCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | C(CCCCC)OC1=CC=C(N)C=C1.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)(C)N(C(C)C)CC>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)OCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:31][cH:32]1.Cl[c:13]1[n:14][cH:15][c:16]([F:17])[c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[n:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[n... | CCCCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CCCCCCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | C(CO)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 23.1 | [{"value": 23.0, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)OCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.1, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)OCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | To a magnetically stirred solution of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine (0.25 g, 0.89 mmol) in ethylene glycol (3.0 mL) under nitrogen at room temperature was added N,N-diisopropylethylamine (0.12 g, 0.89 mmol) followed by 4-hexyloxyaniline (0.27 g, 1.4 mmol). The reaction mixture was hea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | C(CO)O | 170 | null | CCCCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>C(CO)O>CCCCCCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad37ea37bbcd42fa81e2d8271a7d9c1b | CCCCOc1ccc(N)cc1.CCN(C(C)C)C(C)C.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCCCOc1ccc(Nc2cc(Nc3ccc4c(c3)OCCO4)c(F)cn2)cc1 | C(CCC)OC1=CC=C(N)C=C1.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)(C)N(C(C)C)CC>>C(CCC)OC1=CC=C(C=C1)NC1=NC=C(C(=C1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]1.CCN(C(C)C)C(C)[CH3:12].Cl[c:11]1n[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[c:25]([F:26])[cH:27][n:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][c:13]([N... | CCCCOc1ccc(N)cc1.CCN(C(C)C)C(C)C.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CCCCOc1ccc(Nc2cc(Nc3ccc4c(c3)OCCO4)c(F)cn2)cc1 | null | null | C(CO)O | Heteroatom Alkylation and Arylation | OtherReaction | ac8434f37766d1dc375cf703d914f347e98abd5c6a037689067b7f085ac9dbe9 | e64bf82d919771531f8c95b89789db7e2c93fce864ccaad7e532706b977151ca | c1ccc(Nc2cc(Nc3ccc4c(c3)OCCO4)ccn2)cc1 | C-C-N(-C(-C)-C)-C(-C)-[CH3;D1;+0:1].Cl-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5](-[F;D1;H0:6]):[c;H0;D3;+0:7](-[#7:8]-[c:9]):n:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:6]-[c:5]1:[c:4]:[#7;a:3]:[c;H0;D3;+0:2](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[cH;D2;+0:1]:[c;H0;D3;+0:7]:1-[#7:8]-[c:9] | 49.4 | [{"value": 49.0, "product": "C(CCC)OC1=CC=C(C=C1)NC1=NC=C(C(=C1)NC1=CC2=C(C=C1)OCCO2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.4, "product": "C(CCC)OC1=CC=C(C=C1)NC1=NC=C(C(=C1)NC1=CC2=C(C=C1)OCCO2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 185 | CELSIUS | null | null | To a magnetically stirred solution of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine (0.25 g, 0.89 mmol) in ethylene glycol (3.0 mL) under nitrogen at room temperature was added N,N-diisopropylethylamine (0.12 g, 0.89 mmol) followed by 4-butoxyaniline (0.18 g, 1.1 mmol). The reaction mixture was heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Tertiary amine | Secondary amine | c1cncnc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccc2c(c1)OCCO2 | HCl | C(CO)O | 185 | null | CCCCOc1ccc(N)cc1.CCN(C(C)C)C(C)C.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>C(CO)O>CCCCOc1ccc(Nc2cc(Nc3ccc4c(c3)OCCO4)c(F)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-609fa592601d4c4c9063b42dde6433de | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>>CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | C1OC=2C=C(N)C=CC2OC1.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)F.C(C)N(C(C)C)C(C)C>>C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2 | Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:28][cH:27]2)[c:25]([F:26])[cH:24][n:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[O... | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2 | CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | null | null | C(CO)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 60 | [{"value": 60.0, "product": "C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.1, "product": "C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | null | null | To a solution of 2-chloro-N4-(4-ethyloxyphenyl)-5-fluoro-4-pyrimidineamine (0.25 g, 0.93 mmol) in ethylene glycol (3 mL) under nitrogen at room temperature was added i-Pr2EtN, 0.93 mmol) followed by 3,4-ethylenedioxyaniline (0.17 g, 1.12 mmol). The reaction mixture was heated to 200° C. for 5 h and then cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | C(CO)O | 200 | null | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>C(CO)O>CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2a0927572eb48739647531b1d114bd5 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(CC(O2)C(=O)O)C1.C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.[Li+].[OH-]>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)O)C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22]4)[O:23][CH2:24][CH2:25][O:26]5)[n:27]3)[cH:28][cH:29][c:30]2[o:31]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c... | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3occc3c2)n1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-(2,3-dihydro-2-carboxybenzofuran-5-yl)-2,4-pyrimidinediamine, N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine and LiOH were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-carboxy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | Other | null | null | null | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1>>O=C(O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcaf9e2999a94fe8af70164c56c26c0a | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1>>Fc1cnc(Nc2ccc(C(F)(F)F)cc2)nc1Nc1ccc(C(F)(F)F)cc1 | ClC1=NC=C(C(=N1)Cl)F.FC(C1=CC=C(N)C=C1)(F)F>>FC(C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(F)(F)F)F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18](Cl)[n:6]1.[cH:7]1[cH:21][c:20]([NH2:19])[cH:29][cH:28][c:23]1[C:24]([F:12])([F:13])[F:14]>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[n:17][c:18]1[NH:19][c:20]1[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH... | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1 | Fc1cnc(Nc2ccc(C(F)(F)F)cc2)nc1Nc1ccc(C(F)(F)F)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 66682a52abce76f54fa78b86775e047d4fa631016123cccef84cf38328628f5e | 267a067712961bc46fc81ae4aab19c60779b254d77a4ff4b5e386191547d1b46 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[F;H0;D1;+0:8]-[C;H0;D4;+0:9](-[F;H0;D1;+0:10])(-[F;H0;D1;+0:11])-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15](-[NH2;D1;+0:16]):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:2]-[c;H0;D3;+0:18]2... | null | [] | null | null | null | null | In a manner similar to the preparation of N2-N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidineamine, the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-trifluoromethylaniline gave N2,N4-bis(4-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.06 (bs, 1H), 7.75 (d, 2H, J=9 Hz), 7.67 (d, 2H, J=9... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Primary amine | Trifluoro group.Trifluoro group.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1>>Fc1cnc(Nc2ccc(C(F)(F)F)cc2)nc1Nc1ccc(C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8008e7e940a4734b30475e8bfd28ed2 | CCOC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OCC)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C)OC(=O)C=1C=C(N)C=CC1>>C(C)OC(=O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)OCC)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:29][c:19]([NH2:18])[cH:20][cH:7][cH:31]1.Cl[c:12]1[n:11][c:17](Cl)[c:15]([F:16])[cH:14][n:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][c:23]([C:24](=[O:25])[O:26][CH2:27]... | CCOC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl | CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OCC)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8f0fa5f8519414e949eb8bafeb20d028d1ee2f0dfa005f0c191ecb23ea6a7bcc | 6552361de42d161b0a08a553c1d23825d7c8b38b72c3b0e48e062893d39afff9 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-Cl):[n;H0;D2;+0:7]:1.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[c:14](-[NH2;D1;+0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C:19]-[c:20]1:[c:21]:[c:22]:[cH;D2;+0:16]:[c:14](-[NH;D2;+0:15]-[c;H0;D3;+0:6]2:[#7;a:23]:[c;... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,4-dichloro-5-fluoropyrimidine and 3-ethoxycarbonylaniline gave N2,N4-bis(3-ethoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 26.55 min.; purity: 100%; MS (m/e): 425 (MH+).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Primary amine | Ester.Ester.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CCOC(=O)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3cccc(C(=O)OCC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7db684627784c53a8481ff4d9c67cfd | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)OC(=O)C=1C=C(N)C=CC1>>C(C)OC(=O)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:30]1.Oc1cccc(N[c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]4[c:23]([cH:24]3)[O:25][CH2:26][CH2:27][O:28]4)[n:29]2)c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]... | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-ethoxycarbonylaniline gave N2-(3-ethoxycarbonylphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CCOC(=O)c1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCOC(=O)c1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2b76137a03d457ab2014154caeeea84 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cccc(-c4nnc(-c5ccccc5)o4)c3)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=C(O1)C1=CC=CC=C1)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)C1=NN=C(O1)C1=CC=CC=C1 | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19](-[c:20]3[n:21][n:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[o:30]3)[cH:31]2)[n:32]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:33]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:1... | Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3cccc(-c4nnc(-c5ccccc5)o4)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3cccc(-c4nnc(-c5ccccc5)o4)c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-5-fluoro-N4-[3-(2-phenyl-1,3,4-oxadiazol-5-yl)phenyl]-4-pyrimidineamine gave 5-fluoro-N2-(3-hydroxyphenyl)-N4-[3-(2-phenyl-1,3,4-oxadiazol-5-yl)ph... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1nnco1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cccc(-c4nnc(-c5ccccc5)o4)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-beabc770492344409378d46175b4f175 | Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cc4c(F)c(F)c3OCO4)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=C2C(=C(C(=C1)OCO2)F)F)F>>FC=1C2=C(C=C(C1F)OCO2)NC2=NC(=NC=C2F)NC2=CC(=CC=C2)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][c:17]3[c:18]([F:19])[c:20]([F:21])[c:22]2[O:23][CH2:24][O:25]3)[n:26]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:27]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][c:17]4[c:18]([F:19])[c:20]([F... | Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3cc4c(F)c(F)c3OCO4)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3cc4ccc3OCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine gave N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cc2ccc1OCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cc4c(F)c(F)c3OCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fba94f1fe5143779458bd3b9a104305 | Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(F)(F)F)c3)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)OC(F)(F)F)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC1=CC(=CC=C1)OC(F)(F)F | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25]2)[n:26]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:27]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][C... | Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(F)(F)F)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-5-fluoro-N4-(3-trifluoromethoxyphenyl)-4-pyrimidineamine gave 5-fluoro-N2-(3-hydroxyphenyl)-N4-(3-trifluoromethoxyphenyl)-2,4-pyrimidinediamine. 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(F)(F)F)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f53e38ef8fe6431eac220936564f4d61 | COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)n1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC=1C(=NC(=CC1)OC)OC)F>>COC1=NC(=CC=C1NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O)OC | Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:26][c:23]2[O:24][CH3:25])[c:21]([F:22])[cH:20][n:19]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]3)[n:19][cH:20][c:21]2... | COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1.Nc1cccc(O)c1 | COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-N4-(2,6-dimethoxypyridin-3-yl)-5-fluoro-4-pyrimidineamine gave N4-(2,6-dimethoxypyridin-3-yl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87a4139a7a404c8a856bc7d2823e29fc | Cc1ccc(Nc2nc(Cl)ncc2F)nc1.Nc1cccc(O)c1>>Cc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)nc1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=NC=C(C=C1)C)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC1=NC=C(C=C1)C | Cl[c:9]1[n:8][c:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:23][n:22]2)[c:20]([F:21])[cH:19][n:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]3)[n:18][cH:19][c:20]2[F:21])[n:22][cH:23]1 | Cc1ccc(Nc2nc(Cl)ncc2F)nc1.Nc1cccc(O)c1 | Cc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)nc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccccn3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-5-fluoro-N4-(5-methylpyridin-2-yl)-4-pyrimidineamine gave 5-fluoro-N2-(3-hydroxyphenyl)-N4-(5-methylpyridin-2-yl)-2,4-pyrimidinediamine. 1H NMR (D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Cc1ccc(Nc2nc(Cl)ncc2F)nc1.Nc1cccc(O)c1>>Cc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a93d1e9d264a44f1955d7c77c4495c26 | Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)nc3)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC=1C=NC(=CC1)Cl)F>>ClC1=CC=C(C=N1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]2)[n:22]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]3)[n:22]2)[cH:23]1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)nc3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-N4-(6-chloropyridin-3-yl)-5-fluoro-4-pyrimidineamine gave N4-(6-chloropyridin-3-yl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)nc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-157355b22599432d81f102ebd099cd35 | Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4ncccc4c3)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC=1C=C2C=CC=NC2=CC1)F>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NC=1C=C2C=CC=NC2=CC1 | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[n:19][cH:20][cH:21][cH:22][c:23]3[cH:24]2)[n:25]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[n:19][cH:20][cH:21][cH... | Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3ccc4ncccc4c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4ncccc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-5-fluoro-N4-(quinolin-6-yl)-4-pyrimidineamine gave 5-fluoro-N2-(3-hydroxyphenyl)-N4-(quinolin-6-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2ncccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4ncccc4c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e184b7bf4bf475692cde15d4a367bc1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)cn1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)cn3)n2)c1 | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=NC=C(C=C1)Cl)F>>ClC=1C=CC(=NC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][n:21]2)[n:22]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][n:21]3)[n:22]2)[cH:23]1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)cn1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)cn3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccccn3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-N4-(5-chloropyridin-2-yl)-5-fluoro-4-pyrimidineamine gave N4-(5-chloropyridin-2-yl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc(Cl)cn1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc(Cl)cn3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a33def208d34871be059d7cda64f9ac | COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl.Nc1cccc(O)c1>>COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)cc1Cl | OC=1C=C(N)C=CC1.ClC1=NC=C(C(=N1)NC1=C(C=C(C(=C1)OC)Cl)OC)F>>ClC1=CC(=C(C=C1OC)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O)OC | Cl[c:9]1[n:8][c:7]([NH:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([Cl:27])[cH:25][c:22]2[O:23][CH3:24])[c:20]([F:21])[cH:19][n:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]3)[n:18][cH:19][c:20... | COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl.Nc1cccc(O)c1 | COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 3-hydroxyaniline with 2-chloro-N4-(4-chloro-2,5-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine gave N4-(4-chloro-2,5-dimethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinedia... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl.Nc1cccc(O)c1>>COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)c(OC)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4eff15322d4b4a14b0667ba713d39af3 | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2o1 | NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)Cl)F>>ClC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:26][cH:27][c:28]2[o:29]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]... | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 5-amino-2-methoxycarbonylbenzofuran with 2-chloro-N4-(4-chlorophenyl)-5-fluoro-4-pyrimidineamine gave N4-(4-chlorophenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)cc1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)cc4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd019cfc85394f688c2f530ccd871c3e | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2o1 | NC=1C=CC2=C(C=C(O2)C(=O)OC)C1.ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)Cl)Cl)F>>ClC=1C=C(C=CC1Cl)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:27][cH:28][c:29]2[o:30]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]2)[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:15])[c:16]([NH:1... | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 5-amino-2-methoxycarbonylbenzofuran with 2-chloro-N4-(3,4-dichlorophenyl)-5-fluoro-4-pyrimidineamine gave N4-(3,4-dichlorophenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc2cc(N)ccc2o1.Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(Cl)c(Cl)c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d1df08c734f4577a24352f2be2ad4f6 | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC(=O)C=1C=C(N)C=C(C1)C(F)(F)F>>FC=1C(=NC(=NC1)NC1=CC(=CC(=C1)C(F)(F)F)C(=O)OC)NC1=CC(=CC=C1)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]2)[n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:... | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-methoxycarbonyl-5-trifluoromethylaniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-methoxycarbonyl-5-trifluorometh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COC(=O)c1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2e791390c1a479f8b45266aae2fa98c | COc1cc(Cl)c(OC)cc1N.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c(OC)cc1Cl | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=CC(=C(N)C=C1OC)OC>>ClC1=CC(=C(C=C1OC)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:22]([O:23][CH3:24])[cH:25][c:26]1[Cl:27].Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]2)[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20... | COc1cc(Cl)c(OC)cc1N.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c(OC)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 4-chloro-2,5-dimethoxyaniline gave N2-(4-chloro-2,5-dimethoxyphenyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinedi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1cc(Cl)c(OC)cc1N.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1cc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c(OC)cc1Cl |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.