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-e34860cbd3f740faade1818dd06ff3c0 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | ClC1=NC=C(C(=N1)Cl)F.N1N=NN=C1C=1C=C(N)C=CC1.O>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=NN1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | null | null | CO.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncn2)cc(-c2nnn[nH]2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | 60 | CELSIUS | null | null | A reaction mixture containing 2,4-dichloro-5-fluoro-pyrimidine (1.2 equivalents) and 3-(tetrazol-5-yl)aniline (1 equivalents) in methanol:water (1:1; v/v) was heated at 60° C. for 24 h. Upon dilution with water and acidification, the solid formed was filtered, washed with water, dried and analyzed to give 2-chloro-5-fl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnn[nH]1 | HCl | CO.O | 60 | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>CO.O>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c7994eb7921430fa3ff914a70686aab | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | ClC1=NC=C(C(=N1)Cl)F.N1N=NN=C1C=1C=C(N)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=NN1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | null | null | CO.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncn2)cc(-c2nnn[nH]2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | A reaction mixture containing 2,4-dichloro-5-fluoro-pyrimidine (1.2 equivalents) and 3-(tetrazol-5-yl)aniline (1 equivalents) in methanol:water (1:1; v/v) was heated at 60° C. for 24 h. Upon dilution with water and acidification, the solid formed was filtered, washed with water, dried and analyzed to give 2-chloro-5-fl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnn[nH]1 | HCl | CO.O | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>CO.O>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d23a43c82e945a5af2daf80a70466fc | COc1cc(Cl)c(OC)cc1N.Fc1cnc(Cl)nc1Cl>>COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl | ClC1=NC=C(C(=N1)Cl)F.COC1=C(N)C=C(C(=C1)Cl)OC>>ClC1=NC=C(C(=N1)NC1=C(C=C(C(=C1)OC)Cl)OC)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:15]([O:16][CH3:17])[cH:18][c:19]1[Cl:20].Cl[c:7]1[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]1[F:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]2[F:14])[c:15]([O:16][CH3:17])[cH:18][c:19]1[Cl:20] | COc1cc(Cl)c(OC)cc1N.Fc1cnc(Cl)nc1Cl | COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 2,5-dimethoxy-4-chloroaniline gave 2-chloro-N4-(2,5-dimethoxy-4-chlorophenyl)-5-fluoro-4-pyrimidineamine. LCMS: purity: 97%; MS (m/e): 316 (M-2H) and 320 (M+2H).
... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | COc1cc(Cl)c(OC)cc1N.Fc1cnc(Cl)nc1Cl>>COc1cc(Nc2nc(Cl)ncc2F)c(OC)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-40475370ce7645e2b16d58aa07ea1bde | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Cl>>COC(=O)c1cc(Nc2nc(Cl)ncc2F)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.COC(=O)C=1C=C(N)C=C(C1)C(F)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=CC(=C1)C(F)(F)F)C(=O)OC)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]1.Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]2[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]1 | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Cl | COC(=O)c1cc(Nc2nc(Cl)ncc2F)cc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-methoxycarbonyl-5-trifluoromethylaniline gave 2-chloro-5-fluoro-N4-(3-methoxycarbonyl-5-trifluoromethylphenyl)-4-pyrimidineamine. 1H NMR (CD3OD): δ 8.60 (s, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | COC(=O)c1cc(N)cc(C(F)(F)F)c1.Fc1cnc(Cl)nc1Cl>>COC(=O)c1cc(Nc2nc(Cl)ncc2F)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d78f6127a3fc4c4bad4b3ccf6cf09b7e | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnc(-c3ccccc3)o2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1 | ClC1=NC=C(C(=N1)Cl)F.C1(=CC=CC=C1)C=1OC(=NN1)C=1C=C(N)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=C(O1)C1=CC=CC=C1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[o:25]2)[cH:26]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][... | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnc(-c3ccccc3)o2)c1 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nnc(-c3cccc(Nc4ccncn4)c3)o2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-(2-phenyl-1,3,4-oxadiazol-5-yl)aniline gave 2-chloro-5-fluoro-N4-[3-(2-phenyl-1,3,4-oxadiazol-5-yl)phenyl)-4-pyrimidineamine. 1H NMR (DMSO-d6): δ 10.28 (s, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnco1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnc(-c3ccccc3)o2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnc(-c3ccccc3)o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b6886e6d30342f5ae8727dd773cedc5 | CCOC(=O)C=C1NN=C(c2cccc(N)c2)O1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C=C1NN=C(c2cccc(Nc3nc(Cl)ncc3F)c2)O1 | ClC1=NC=C(C(=N1)Cl)F.C(C)OC(=O)C=C1OC(=NN1)C=1C=C(N)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NNC(O1)=CC(=O)OCC)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[NH:8][N:9]=[C:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([NH2:16])[cH:25]2)[O:26]1.Cl[c:17]1[n:18][c:19]([Cl:20])[n:21][cH:22][c:23]1[F:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[NH:8][N:9]=[C:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c:19]([Cl:20])[n:... | CCOC(=O)C=C1NN=C(c2cccc(N)c2)O1.Fc1cnc(Cl)nc1Cl | CCOC(=O)C=C1NN=C(c2cccc(Nc3nc(Cl)ncc3F)c2)O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | [CH]=C1NN=C(c2cccc(Nc3ccncn3)c2)O1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-(2-ethoxycarbonylmethylene-1,3,4-oxadiazol-5-yl)aniline gave 2-chloro-N4-[3-(2-ethoxycarbonylmethylene-1,3,4-oxadiazol-5-yl)phenyl]-5-fluoro-4-pyrimidineamine. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1=NNCO1.c1ccccc1.c1cncnc1 | HCl | null | null | null | CCOC(=O)C=C1NN=C(c2cccc(N)c2)O1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C=C1NN=C(c2cccc(Nc3nc(Cl)ncc3F)c2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36ab29691e014e9c870a02087e57234e | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)cc1>>Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)cc1 | ClC1=NC=C(C(=N1)Cl)F.FC(OC1=CC=C(N)C=C1)(F)F>>ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OC(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)cc1 | Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-trifluoromethoxyaniline gave 2-chloro-5-fluoro-N4-(4-trifluoromethoxyphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.11 (d, 1H, J=2.1 Hz), 7.68 (dd, 2H, J=2.4 an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)cc1>>Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbf63625ffcf450c8d31675b3118a7f2 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1>>Fc1cnc(Cl)nc1Nc1ccc(C(F)(F)F)cc1 | ClC1=NC=C(C(=N1)Cl)F.FC(C1=CC=C(N)C=C1)(F)F>>ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1 | Fc1cnc(Cl)nc1Nc1ccc(C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-trifluoromethylaniline gave 2-chloro-5-fluoro-N4-(4-trifluoromethylphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.15 (d, 2.1 Hz), 7.80 (d, 2H, J=7.1 Hz), 7.66 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)cc1>>Fc1cnc(Cl)nc1Nc1ccc(C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abdf8e2de2b24488bc7d06e476c4f206 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.ClC1=C(C=C(N)C=C1)C(F)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)Cl)C(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-chloro-3-trifluoromethylaniline gave 2-chloro-N4-(4-chloro-3-trifluoromethylphenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.15 (d, 1H, J=2.1 Hz), 7.96 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cae166816a24b119d8b2e7d979c1f4e | COc1ccc(N)cn1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2nc(Cl)ncc2F)cn1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=NC(=CC1)OC>>ClC1=NC=C(C(=N1)NC=1C=NC(=CC1)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][n:17]1.Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[cH:16][n:17]1 | COc1ccc(N)cn1.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2nc(Cl)ncc2F)cn1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-amino-6-methoxypyridine gave 2-chloro-5-fluoro-N4-(6-methoxypyridin-3-yl)-4-pyrimidineamine. 1H NMR (CD3OD): δ 8.39 (d, 1H, J=3.0 Hz), 8.10 (d, 1H, J=3.6 Hz), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HCl | null | null | null | COc1ccc(N)cn1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2nc(Cl)ncc2F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e84bc9fb1c340feb074cea318cf1456 | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(F)c1>>Fc1ccc(Nc2nc(Cl)ncc2F)cc1F | ClC1=NC=C(C(=N1)Cl)F.FC=1C=C(N)C=CC1F>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)F)F)F | Cl[c:7]1[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]1[F:14].[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:15][c:16]1[F:17]>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]2[F:14])[cH:15][c:16]1[F:17] | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(F)c1 | Fc1ccc(Nc2nc(Cl)ncc2F)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3,4-difluoroaniline gave 2-chloro-N4-(3,4-difluorophenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.10 (d, 1H, J=2.1 Hz), 7.72 (m, 1H), 7.22 (m, 2H), 6.95 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(F)c1>>Fc1ccc(Nc2nc(Cl)ncc2F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-102e957aa4704ef09ae93b99f220c92c | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(Cl)c1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1 | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=CC1Cl>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)Cl)Cl)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(Cl)c1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3,4-dichloroaniline gave 2-chloro-N4-(3,4-dichlorophenyl)-5-fluoro-4-pyrimidineamine. LCMS: purity: 95%; MS (m/e): 294 (M+2H).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(Cl)c1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd85cd52ec2b4971ad06a0902775a610 | Cc1cccc(N)n1.Fc1cnc(Cl)nc1Cl>>Cc1cccc(Nc2nc(Cl)ncc2F)n1 | ClC1=NC=C(C(=N1)Cl)F.NC1=NC(=CC=C1)C>>ClC1=NC=C(C(=N1)NC1=NC(=CC=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[n:16]1.Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[n:16]1 | Cc1cccc(N)n1.Fc1cnc(Cl)nc1Cl | Cc1cccc(Nc2nc(Cl)ncc2F)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 2-amino-6-methylpyridine gave 2-chloro-5-fluoro-N4-(6-methylpyridin-2-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.23 (s, 1H), 8.19 (s, 1H), 8.12 (d, 1H, J=3 Hz), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HCl | null | null | null | Cc1cccc(N)n1.Fc1cnc(Cl)nc1Cl>>Cc1cccc(Nc2nc(Cl)ncc2F)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a6bd1d31c4c49c4827bf7fe793f706f | COc1ccc(N)c(OC)n1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C(=NC(=CC1)OC)OC>>ClC1=NC=C(C(=N1)NC=1C(=NC(=CC1)OC)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:16]([O:17][CH3:18])[n:19]1.Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[c:16]([O:17][CH3:18])[n:19]1 | COc1ccc(N)c(OC)n1.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[#8:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#8:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[c:14] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-amino-2,6-dimethoxypyridine gave 2-chloro-N4-(2,6-dimethoxypyridin-3-yl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.57 (d, 1H, J=8.7 Hz), 8.02 (d, 1H, J=2.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HCl | null | null | null | COc1ccc(N)c(OC)n1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2nc(Cl)ncc2F)c(OC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0738f6b11ba64057bcfe2cdfb6feae41 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)nc1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=NC(=CC1)Cl>>ClC1=NC=C(C(=N1)NC=1C=NC(=CC1)Cl)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[n:15][cH:16]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[n:15][cH:16]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)nc1 | Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Nc2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-amino-6-chloropyridine gave 2-chloro-N4-(6-chloropyridin-3-yl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.53 (d, 1H, J=3 Hz), 8.25 (dd, 1H, J=3 and 9 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)nc1>>Fc1cnc(Cl)nc1Nc1ccc(Cl)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c43fc2dc04d41dda8ede4faf289c6bb | Cc1ccnc(N)c1.Fc1cnc(Cl)nc1Cl>>Cc1ccnc(Nc2nc(Cl)ncc2F)c1 | ClC1=NC=C(C(=N1)Cl)F.NC1=NC=CC(=C1)C>>ClC1=NC=C(C(=N1)NC1=NC=CC(=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[cH:16]1.Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[cH:16]1 | Cc1ccnc(N)c1.Fc1cnc(Cl)nc1Cl | Cc1ccnc(Nc2nc(Cl)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 2-amino-4-methylpyridine gave 2-chloro-5-fluoro-N4-(4-methylpyridin-2-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.22 (s, 1H), 8.16 (d, 1H, J=8.4 Hz), 8.13 (d, 1H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1 | HCl | null | null | null | Cc1ccnc(N)c1.Fc1cnc(Cl)nc1Cl>>Cc1ccnc(Nc2nc(Cl)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d372d57841f8477cad3cca22df8251ca | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.FC(OC=1C=C(N)C=CC1)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)OC(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1 | Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-trifluoromethoxyaniline gave 2-chloro-5-fluoro-N4-(3-trifluoromethoxyphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.12 (d, 1H, J=3 Hz), 7.68 (bs, 1H), 7.53 (dd,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1cccc(OC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93f51f2be90f40d3afbb6e8d2b0638fc | Fc1ccc2c(c1F)OCON2.Fc1cnc(Cl)nc1Cl>>Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2 | ClC1=NC=C(C(=N1)Cl)F.FC=1C2=C(NOCO2)C=CC1F>>ClC1=NC=C(C(=N1)NC1=C2C(=C(C(=C1)OCO2)F)F)F | [NH:9]1[c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[c:17]2[O:18][CH2:19][O:20]1.Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][c:12]2[c:13]([F:14])[c:15]([F:16])[c:17]1[O:18][CH2:19][O:20]2 | Fc1ccc2c(c1F)OCON2.Fc1cnc(Cl)nc1Cl | Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 37b8c52ae3dbda39d0b7270468a99f71ee939bd3b766282120e6d06893a02999 | 0774216dd7c64486be2406f31dc7aaa54c721f65f5da0a17ec83e5df781d9f00 | c1cc(Nc2cc3ccc2OCO3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[F;D1;H0:9]-[c:10]1:[c:11]:[c:12]2:[c:13](:[c:14]:[cH;D2;+0:15]:1)-[NH;D2;+0:16]-[O;H0;D2;+0:17]-[C:18]-[#8:19]-2>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:13]2:[c:14]:[c;H0;D3;+0:15]3:[c:1... | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3,4-difluoromethylenedioxyaniline gave 2-chloro-N4-(3,4-difluoromethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.09 (d, 1H, J=3 Hz), 7.70 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Ether.Secondary amine | c1ccc2c(c1)NOCO2.c1cncnc1 | c1cncnc1.c1cc2ccc1OCO2 | c1cncnc1.c1cc2ccc1OCO2 | HCl | null | null | null | Fc1ccc2c(c1F)OCON2.Fc1cnc(Cl)nc1Cl>>Fc1cnc(Cl)nc1Nc1cc2c(F)c(F)c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-079272bdad4e4419a6d9aacdcd362bd7 | Fc1cnc(Cl)nc1Cl.Nc1ccc2ncccc2c1>>Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C2C=CC=NC2=CC1>>ClC1=NC=C(C(=N1)NC=1C=C2C=CC=NC2=CC1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[cH:19]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc2ncccc2c1 | Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2ccc(Nc3ccncn3)cc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 6-aminoquinoline gave 2-chloro-5-fluoro-N4-(quinolin-6-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.02 (dd, 1H, J=2.7 Hz), 8.00 (dd, 1H, J=2.4 Hz), 7.73 (d, 1H, J=9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2ncccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2ncccc2c1>>Fc1cnc(Cl)nc1Nc1ccc2ncccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7160a7a0c5b458b8ae3c2d684262709 | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)c(Cl)c1>>Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1 | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=CC1OC(F)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC(F)(F)F)Cl)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[c:19]([Cl:20])[cH:21]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[c:19]([Cl:20])[cH:21]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)c(Cl)c1 | Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-chloro-4-trifluoromethoxyaniline gave 2-chloro-N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.15 (d, 1H, J=3.0 Hz), 7.86... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(OC(F)(F)F)c(Cl)c1>>Fc1cnc(Cl)nc1Nc1ccc(OC(F)(F)F)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e095b83dad0348b6aa822b169848a514 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)CNCC2>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)CN(c1nc(Cl)ncc1F)CC2 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2CCNCC2=C1>>ClC1=NC=C(C(=N1)NC1=CC=C2CCN(CC2=C1)C1=NC(=NC=C1F)Cl)F | [F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[Cl:21].[NH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH2:16][NH:17][CH2:26][CH2:27]2>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH2:16][N:17]([c:18]1[n:19][c:20]([Cl:21])[n:22][cH:23][c:24]1[F:25])[CH2:26][CH2:27... | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)CNCC2 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)CN(c1nc(Cl)ncc1F)CC2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 521563826c9888cd06384ef5adaaf3e1702ddcdefcb77a86c0bac536a60cb6be | 0d7b24bdf97a7d48a31a6e19fff1b868b6461fb8bd155c7b6d75b265588cafa5 | c1cc(Nc2ccc3c(c2)CN(c2ccncn2)CC3)ncn1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9].[Cl;D1;H0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14](-[F;D1;H0:15]):[c;H0;D3;+0:16](-[Cl;H0;D1;+0:17]):[#7;a:18]:1>>[#7;a:19]:[c:20](-[Cl;H0;D1;+0:17]):[#7;a:21]:[c:22](-[N;H0;D3;+0:3](-[C:4]-[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[c;H0;D3;+0:16]1:[#7;a:18]:[c:11... | null | [] | null | null | null | null | In a like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 7-amino-1,2,3,4-tetrahydroisoquinoline were reacted to provide 2-chloro-N4-[2-(2-chloro-5-fluoropyrimidin-4-yl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-5-fluoro-4-pyrimidineamine. 1H NMR (CD... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine | Aromatic halide.Aromatic halide.Secondary amine.Tertiary amine | c1cncnc1.c1ccc2c(c1)CCNC2 | c1cncnc1.c1ccc2c(c1)CC[NH]C2.c1cncnc1 | c1cncnc1.c1ccc2c(c1)CC[NH]C2.c1cncnc1 | Other | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)CNCC2>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)CN(c1nc(Cl)ncc1F)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c455497083a24354a5bb5beb9c97ec68 | CC(C)(C)OC(=O)N1CCc2ccc(N)cc2C1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2CCN(CC2=C1)C(=O)OC(C)(C)C>>ClC1=NC=C(C(=N1)NC1=CC=C2CCN(CC2=C1)C(=O)OC(C)(C)C)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:24][c:25]2[CH2:26]1.Cl[c:16]1[n:17][c:18]([Cl:19])[n:20][cH:21][c:22]1[F:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([NH:15][c:16]3[n:17][c:18]([Cl:19])... | CC(C)(C)OC(=O)N1CCc2ccc(N)cc2C1.Fc1cnc(Cl)nc1Cl | CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)CNCC3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 7-amino-2-(t-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline were reacted to provide 2-chloro-5-fluoro-N4-[2-(t-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-4-pyrimidineamin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CC[NH]C2.c1cncnc1 | HCl | null | null | null | CC(C)(C)OC(=O)N1CCc2ccc(N)cc2C1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-59f168c3fc8e423caa64fe18919c1d50 | CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)CNCC2 | ClC1=NC=C(C(=N1)NC1=CC=C2CCN(CC2=C1)C(=O)OC(C)(C)C)F>>ClC1=NC=C(C(=N1)NC1=CC=C2CCNCC2=C1)F | CC(C)(C)OC(=O)[N:17]1[CH2:16][c:14]2[c:13]([cH:12][cH:11][c:10]([NH:9][c:8]3[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]3)[cH:15]2)[CH2:19][CH2:18]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[CH2:16][NH:17][CH2:18][CH2:19]2 | CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)CNCC2 | null | null | FC(C(=O)O)(F)F.ClCCl | Reduction | Boc amine deprotection | acbecc2fe3298c7b9fe71052b8ac801d3dd977be469b0445320e26e414cad87c | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(Nc2ccc3c(c2)CNCC3)ncn1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | A solution of 2-chloro-5-fluoro-N4-[2-(t-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-4-pyrimidineamine in 40% trifluoroacetic acid/dichloromethane was stirred at rt for 30 min. Removal of the solvent left an oily residue which was suspended in water, made basic with NaHCO3, and extracted with ethyl acetate. Pur... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1cncnc1.c1ccc2c(c1)CCNC2 | HO- | FC(C(=O)O)(F)F.ClCCl | null | null | CC(C)(C)OC(=O)N1CCc2ccc(Nc3nc(Cl)ncc3F)cc2C1>FC(C(=O)O)(F)F.ClCCl>Fc1cnc(Cl)nc1Nc1ccc2c(c1)CNCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78debc56c6154660997194a2c3d8185f | Cc1ccc(N)cc1C(F)(F)F.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2nc(Cl)ncc2F)cc1C(F)(F)F | ClC1=NC=C(C(=N1)Cl)F.CC1=C(C=C(N)C=C1)C(F)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C)C(F)(F)F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:15][c:16]1[C:17]([F:18])([F:19])[F:20].Cl[c:7]1[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]1[F:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]2[F:14])[cH:15][c:16]1[C:17]([F:18])([F:19])[F:20] | Cc1ccc(N)cc1C(F)(F)F.Fc1cnc(Cl)nc1Cl | Cc1ccc(Nc2nc(Cl)ncc2F)cc1C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 4-methyl-3-trifluoromethylaniline were reacted to provide 2-chloro-5-fluoro-N4-(4-methyl-3-trifluoromethylphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.10 (d, 1H, J=3.0 Hz), 7.85... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Cc1ccc(N)cc1C(F)(F)F.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2nc(Cl)ncc2F)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3885c6b64e7b450081229262e8eee846 | Cc1cc(N)ccc1F.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)ccc1F | ClC1=NC=C(C(=N1)Cl)F.FC1=C(C=C(N)C=C1)C>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)F)C)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:14][cH:15][c:16]1[F:17].Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]1[F:13]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]2[F:13])[cH:14][cH:15][c:16]1[F:17] | Cc1cc(N)ccc1F.Fc1cnc(Cl)nc1Cl | Cc1cc(Nc2nc(Cl)ncc2F)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 4-fluoro-3-methylaniline were reacted to provide 2-chloro-5-fluoro-N4-(4-fluoro-3-methylphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.06 (d, 1H, J=2.4 Hz), 7.48-7.43 (m, 1H), 7.3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Cc1cc(N)ccc1F.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84153d744a9a4d92990b4188e0ea5dfb | CCOC(=O)C1CCN(Cc2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C1CCN(Cc2cccc(Nc3nc(Cl)ncc3F)c2)CC1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(CN2CCC(CC2)C(=O)OCC)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)CN1CCC(CC1)C(=O)OCC)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([NH2:16])[cH:25]2)[CH2:26][CH2:27]1.Cl[c:17]1[n:18][c:19]([Cl:20])[n:21][cH:22][c:23]1[F:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c... | CCOC(=O)C1CCN(Cc2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl | CCOC(=O)C1CCN(Cc2cccc(Nc3nc(Cl)ncc3F)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(CN2CCCCC2)cc(Nc2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and ethyl 1-(3-aminobenzyl)piperidine-4-carboxylate were reacted to provide 2-chloro-N4-[3-[[4-(ethoxycarbonyl)piperidino]methyl]phenyl]-5-fluoro-4-pyrimidineamine. LCMS: purity: 97%;... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC[NH]CC1.c1ccccc1.c1cncnc1 | HCl | null | null | null | CCOC(=O)C1CCN(Cc2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C1CCN(Cc2cccc(Nc3nc(Cl)ncc3F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63c4f197961642d7a1de89d8197ac7a3 | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1 | ClC1=NC=C(C(=N1)Cl)F.C(C)OC(=O)C1CCN(CC1)C(=O)C=1C=C(N)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(=O)N1CCC(CC1)C(=O)OCC)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:26]2)[CH2:27][CH2:28]1.Cl[c:18]1[n:19][c:20]([Cl:21])[n:22][cH:23][c:24]1[F:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([NH:17][... | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl | CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1cccc(Nc2ccncn2)c1)N1CCCCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-[[4-(ethoxycarbonyl)piperidino]carbonyl]aniline were reacted to provide 2-chloro-N4-[3-[[4-(ethoxycarbonyl)piperidino]carbonyl]phenyl]-5-fluoro-4-pyrimidineamine. LCMS: purity: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC[NH]CC1.c1ccccc1.c1cncnc1 | HCl | null | null | null | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)C1CCN(C(=O)c2cccc(Nc3nc(Cl)ncc3F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-223aae3009074899a26052bb0df03dc8 | O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21>>OC1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 | C1ON2C(=NC=C(C2(N)OC1)F)NC=1C=CC2=C(C=C(O2)CO)C1.ClC1=NC=C(C(=N1)NC1=CC=C2CCCC(C2=C1)=O)F.CC(C)C[Al]CC(C)C>>ClC1=NC=C(C(=N1)NC1=CC=C2CCCC(C2=C1)O)F | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[F:18])[cH:19][c:20]21>>[OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[F:18])[cH:19][c:20]21 | O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 | OC1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cc(Nc2ccc3c(c2)CCCC3)ncn1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 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, 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-oxonaphthalen-7-yl)-4-pyrimidineamine was reduced with Dibal-H to yield 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-hydroxynaphthalen-7-yl)-4-p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cncnc1 | null | null | null | null | O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21>>OC1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a632cd60852e4685a79804eee9590f33 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)C(=O)CCC2>>O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2CCCC(C2=C1)=O>>ClC1=NC=C(C(=N1)NC1=CC=C2CCCC(C2=C1)=O)F | Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18].[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:19][c:20]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]3[F:18])[cH:19][c:20]21 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)C(=O)CCC2 | O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CCCc2ccc(Nc3ccncn3)cc21 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 7-amino-1-tetralone were reacted to provide 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-oxonaphthalen-7-yl)-4-pyrimidineamine. 1H NMR (DMSO-d6): δ 10.08 (s, 1H), 8.31 (d, 1H, J=3.3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCCC2.c1cncnc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)C(=O)CCC2>>O=C1CCCc2ccc(Nc3nc(Cl)ncc3F)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ea6f74845dc4f7ab92eda6ef185d3b5 | Fc1cnc(Cl)nc1Cl.Nc1cccc(SC(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1cccc(SC(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.FC(SC=1C=C(N)C=CC1)(F)F>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)SC(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([S:15][C:16]([F:17])([F:18])[F:19])[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([S:15][C:16]([F:17])([F:18])[F:19])[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(SC(F)(F)F)c1 | Fc1cnc(Cl)nc1Nc1cccc(SC(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-(trifluoromethylthio) aniline were reacted to provide 2-chloro-5-fluoro-N4-[3-(trifluoromethylthio)phenyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.13 (bs, 1H), 7.92 (bs, 1H), 7.8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(SC(F)(F)F)c1>>Fc1cnc(Cl)nc1Nc1cccc(SC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-925a6742d3404e28b5858a0e00a5a24e | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1>>Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2C=CNC2=C1>>ClC1=NC=C(C(=N1)NC1=CC=C2C=CNC2=C1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][nH:16][c:17]2[cH:18]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][nH:16][c:17]2[cH:18]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1 | Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3cc[nH]c3c2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[c:14] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 6-aminoindole were reacted to provide 2-chloro-5-fluoro-N4-[(1H)-indol-6-yl]-4-pyrimidineamine. LCMS: purity: 92%; MS (m/e): 263(MH+).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1>>Fc1cnc(Cl)nc1Nc1ccc2cc[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42304b282fed4655a64a1eca09bd745b | COC(=O)c1cc2ccc(N)cc2[nH]1.Fc1cnc(Cl)nc1Cl>>COC(=O)c1cc2ccc(Nc3nc(Cl)ncc3F)cc2[nH]1 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2C=C(NC2=C1)C(=O)OC>>ClC1=NC=C(C(=N1)NC1=CC=C2C=C(NC2=C1)C(=O)OC)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:20][c:21]2[nH:22]1.Cl[c:12]1[n:13][c:14]([Cl:15])[n:16][cH:17][c:18]1[F:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][c:14]([Cl:15])[n:16][cH:17][c:18]3[F:19])[cH:20][c:21]2[nH:22]1 | COC(=O)c1cc2ccc(N)cc2[nH]1.Fc1cnc(Cl)nc1Cl | COC(=O)c1cc2ccc(Nc3nc(Cl)ncc3F)cc2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3cc[nH]c3c2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[#7;a:8]:[c:9]:[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7]):[c:13] | null | [] | null | null | null | null | In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 6-amino-2-(methoxycarbonyl)-(1H)-indole were reacted to provide 2-chloro-5-fluoro-N4-[2-(methoxycarbonyl)-(1H)-indol-6-yl]-4-pyrimidineamine which was used without further purific... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2[nH]ccc2c1.c1cncnc1 | HCl | null | null | null | COC(=O)c1cc2ccc(N)cc2[nH]1.Fc1cnc(Cl)nc1Cl>>COC(=O)c1cc2ccc(Nc3nc(Cl)ncc3F)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95e410a26ebb4f0da56b941bf30cdcef | COC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl>>COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC | ClC1=NC=C(C(=N1)Cl)F.N#N.COC(=O)C=1C=C(N)C=CC1OC.ClC1=NC=C(C(=N1)Cl)F.Cl>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)OC)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:17][cH:18][c:19]1[O:20][CH3:21].Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]2[F:16])[cH:17][cH:18][c:19]1[O:20][CH3:21] | COC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl | COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC | null | null | O.CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | 60 | CELSIUS | 30 | MINUTE | The reaction flask equipped with a magnetic stirring bar and a rubber septum (to prevent loss of 2,4-dichloro-5-fluoropyrimidine and N2 inlet was charged with 3-methyloxycarbonyl-4-methoxyaniline (0.88 g, 4.86 mmol), MeOH (3 mL), H2O (7 mL) and 2,4-dichloro-5-fluoropyrimidine (0.81 g, 4.86 mmol). The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | O.CO | 60 | 0.5 | COC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl>O.CO>COC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7376b8a1fa754a378f9811952bd10128 | CNC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl>>CNC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC | ClC1=NC=C(C(=N1)Cl)F.CNC(=O)C=1C=C(N)C=CC1OC>>ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)C(=O)NC)F | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:17][cH:18][c:19]1[O:20][CH3:21].Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]2[F:16])[cH:17][cH:18][c:19]1[O:20][CH3:21] | CNC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl | CNC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-(3-methyloxycarbonyl-4-methoxyphenyl)-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-methylaminocarbonyl-4-methoxyaniline were reacted to produce 2-chloro-5-fluoro-N4-(3-methylaminocarbonyl-4-methoxyphenyl)-4-pyrimidineamine R940305. 1H NMR (DMSO-d6): ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | CNC(=O)c1cc(N)ccc1OC.Fc1cnc(Cl)nc1Cl>>CNC(=O)c1cc(Nc2nc(Cl)ncc2F)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c5614978c314d5e93876ab7b0067eaa | CN(C=C1C=CC=C(N)C1)C(=O)OC(C)(C)C.Fc1cnc(Cl)nc1Cl>>CN(C=C1C=CC=C(Nc2nc(Cl)ncc2F)C1)C(=O)OC(C)(C)C | ClC1=NC=C(C(=N1)Cl)F.C(C)(C)(C)OC(=O)N(C)C=C1CC(N)=CC=C1>>C(C)(C)(C)OC(=O)N(C)C=C1CC(=CC=C1)NC1=NC(=NC=C1F)Cl | [CH3:1][N:2]([CH:3]=[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([NH2:9])[CH2:18]1)[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].Cl[c:10]1[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]1[F:17]>>[CH3:1][N:2]([CH:3]=[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([NH:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[F:17])[CH2:18]1)[C:19](=[O:20... | CN(C=C1C=CC=C(N)C1)C(=O)OC(C)(C)C.Fc1cnc(Cl)nc1Cl | CN(C=C1C=CC=C(Nc2nc(Cl)ncc2F)C1)C(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 94565f710f99d4155675a9f0732ab870d49a7a93dcea19270d443f9bfa287db3 | ccccfb95b8e69084b65046e8e8e3287b0bbdd155a721ff5e70243e9793e85756 | [CH]=C1C=CC=C(Nc2ccncn2)C1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C:8]=[C:9]1-[C:10]-[C:11](-[NH2;D1;+0:12])=[C:13]-[C:14]=[C:15]-1>>[C:8]=[C:9]1-[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:2-[F;D1;H0:7])=[C:13]-[C:14]=[C:15]-1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-(3-methyloxycarbonyl-4-methoxyphenyl)-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-(N-tert-butoxycarbonyl-N-methylaminomethylene)-aniline were reacted to produce N4-[3-(N-tert-butoxycarbonyl-N-methylaminomethylene)-phenyl]-2-chloro-5-fluoro-4-pyrimid... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide | Enamine | c1cncnc1 | c1cncnc1 | C1=CCCC=C1.c1cncnc1 | HCl | null | null | null | CN(C=C1C=CC=C(N)C1)C(=O)OC(C)(C)C.Fc1cnc(Cl)nc1Cl>>CN(C=C1C=CC=C(Nc2nc(Cl)ncc2F)C1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a705881682aa407b93a955e9a61a8d05 | COC1=CC=C(N)CC1=CN(C(=O)OC(C)(C)C)C(C)C.Fc1cnc(Cl)nc1Cl>>COC1=CC=C(Nc2nc(Cl)ncc2F)CC1=CN(C(=O)OC(C)(C)C)C(C)C | ClC1=NC=C(C(=N1)Cl)F.C(C)(C)(C)OC(=O)N(C(C)C)C=C1CC(N)=CC=C1OC>>C(C)(C)(C)OC(=O)N(C(C)C)C=C1CC(=CC=C1OC)NC1=NC(=NC=C1F)Cl | [CH3:1][O:2][C:3]1=[CH:4][CH:5]=[C:6]([NH2:7])[CH2:16][C:17]1=[CH:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH:27]([CH3:28])[CH3:29].Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15]>>[CH3:1][O:2][C:3]1=[CH:4][CH:5]=[C:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[CH2:16][... | COC1=CC=C(N)CC1=CN(C(=O)OC(C)(C)C)C(C)C.Fc1cnc(Cl)nc1Cl | COC1=CC=C(Nc2nc(Cl)ncc2F)CC1=CN(C(=O)OC(C)(C)C)C(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 94565f710f99d4155675a9f0732ab870d49a7a93dcea19270d443f9bfa287db3 | ccccfb95b8e69084b65046e8e8e3287b0bbdd155a721ff5e70243e9793e85756 | [CH]=C1C=CC=C(Nc2ccncn2)C1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C:8]=[C:9]1-[C:10]-[C:11](-[NH2;D1;+0:12])=[C:13]-[C:14]=[C:15]-1>>[C:8]=[C:9]1-[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:2-[F;D1;H0:7])=[C:13]-[C:14]=[C:15]-1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-5-fluoro-N4-(3-methyloxycarbonyl-4-methoxyphenyl)-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-(N-tert-butoxycarbonyl-N-iso-propylaminomethylene)-4-methoxy-aniline were reacted to produce N4-(3-(N-tert-butoxycarbonyl-N-iso-propylaminomethylene)-4-methoxyphenyl)-... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide | Enamine | c1cncnc1 | c1cncnc1 | C1=CCCC=C1.c1cncnc1 | HCl | null | null | null | COC1=CC=C(N)CC1=CN(C(=O)OC(C)(C)C)C(C)C.Fc1cnc(Cl)nc1Cl>>COC1=CC=C(Nc2nc(Cl)ncc2F)CC1=CN(C(=O)OC(C)(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f7a1418416e4e0b8a6e8ad9afaefeb0 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc2c(n1)NC(=O)CO2>>O=C1COc2ccc(Nc3nc(Cl)ncc3F)nc2N1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC=C(C(=N1)Cl)F.NC=1C=CC=2OCC(NC2N1)=O>>ClC1=NC=C(C(=N1)NC=1C=CC=2OCC(NC2N1)=O)F | c1cc2c(cc1N[c:10]1[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]1[F:17])OCCO2.[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:18][c:19]2[NH:20]1>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]3[F:17])[n:18][c:19]2[NH:20]1 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc2c(n1)NC(=O)CO2 | O=C1COc2ccc(Nc3nc(Cl)ncc3F)nc2N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49fa1c8bcf8f8680bcf3c839aefa9cf12322d86ef58184c09a397108941f615c | a713e3fdd0c6b07745ba76404ca21e630fa98570823aec82a6b723a23739e7e7 | O=C1COc2ccc(Nc3ccncn3)nc2N1 | [#7:1]-[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[F;D1;H0:7]-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13]:1-N-c1:c:c:c2:c(:c:1)-O-C-C-O-2>>[#7:1]-[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[c;H0;D3;+0:13]1:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:1-[F;D1;H0:7]):[c:6] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 6-amino-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one were reacted to yield 2-chloro-5-fluoro-N4-[2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one-6-yl]-4-pyrimidineamine. 1H NMR (DMSO-d6): δ 4.6... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Secondary amine | Secondary amine | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1 | c1cnc2c(c1)OCCN2.c1cncnc1 | HO- | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1ccc2c(n1)NC(=O)CO2>>O=C1COc2ccc(Nc3nc(Cl)ncc3F)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-585066ac06a9456f82282ad4f97501c6 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)-n1ccnc1CO2>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)-n1ccnc1CO2 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=CC2=C(N3C(CO2)=NC=C3)C1>>ClC1=NC=C(C(=N1)NC=1C=CC2=C(N3C(CO2)=NC=C3)C1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)-[n:16]1[cH:17][cH:18][n:19][c:20]1[CH2:21][O:22]2>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)-[n:16]1[cH:17][cH:18][n:19][c:20]1[CH2:21][O:22]2 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)-n1ccnc1CO2 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)-n1ccnc1CO2 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)-n2ccnc2CO3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with 8-amino-4H-imidazo[2,1-c][1,4]-benzoxazine to produce 2-chloro-5-fluoro-N-[4H-imidazo[2,1-c][1,4]-benzoxazin-8-yl]-4-pyrimidineamine. 1H NMR (DMSO-d6): 1H NMR (DMSO-d6):... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCc1nccn12 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)-n1ccnc1CO2>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)-n1ccnc1CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef205c69cf2442789b1b6f92cbf4691a | Fc1cnc(Cl)nc1Cl.Nn1cccc1>>Fc1cnc(Cl)nc1Nn1cccc1 | ClC1=NC=C(C(=N1)Cl)F.NN1C=CC=C1>>ClC1=NC=C(C(=N1)NN1C=CC=C1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][n:10]1[cH:11][cH:12][cH:13][cH:14]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][n:10]1[cH:11][cH:12][cH:13][cH:14]1 | Fc1cnc(Cl)nc1Cl.Nn1cccc1 | Fc1cnc(Cl)nc1Nn1cccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn(Nc2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[#7;a:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[#7;a:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with 1-aminopyrrole to produce 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 11.39 (s, 1H), 8.35 (d, 1H, J=3.5 Hz), 6.83 (t, 2H, J=2.3 Hz), 6.07 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cc[nH]c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nn1cccc1>>Fc1cnc(Cl)nc1Nn1cccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06fc53374a9a4c14a3b0d3117e36aa0b | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | ClC1=NC=C(C(=N1)Cl)F.N1N=NN=C1C=1C=C(N)C=CC1.O>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=NN1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | null | null | CO.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncn2)cc(-c2nnn[nH]2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | 60 | CELSIUS | null | null | A reaction mixture containing 2,4-dichloro-5-fluoro-pyrimidine (1.2 equivalents) and 3-(tetrazol-5-yl)aniline (1 equivalents) in methanol:water (1:1; v/v) was heated at 60° C. for 24 h. Upon dilution with water and acidification, the solid formed was fitered, washed with water, dried and analyzed to give 2-chloro-5-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnn[nH]1 | HCl | CO.O | 60 | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>CO.O>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c8aa96df11f4280b9729a215c41aaf6 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | ClC1=NC=C(C(=N1)Cl)F.N1N=NN=C1C=1C=C(N)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=NN=NN1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][nH:19]2)[cH:20]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1 | Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 | null | null | CO.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncn2)cc(-c2nnn[nH]2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | A reaction mixture containing 2,4-dichloro-5-fluoro-pyrimidine (1.2 equivalents) and 3-(tetrazol-5-yl)aniline (1 equivalents) in methanol:water (1:1; v/v) was heated at 60° C. for 24 h. Upon dilution with water and acidification, the solid formed was fitered, washed with water, dried and analyzed to give 2-chloro-5-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1nnn[nH]1 | HCl | CO.O | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2nnn[nH]2)c1>CO.O>Fc1cnc(Cl)nc1Nc1cccc(-c2nnn[nH]2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d242748d91a1445c903f17de450d3fb8 | CCOC(=O)C1CCN(C(=O)c2cccc([N+](=O)[O-])c2)CC1>>CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1 | [N+](=O)([O-])C=1C=C(C(=O)Cl)C=CC1.N1CCC(C(=O)OCC)CC1.C(C)OC(=O)C1CCN(CC1)C(=O)C1=CC(=CC=C1)[N+](=O)[O-]>>C(C)OC(=O)C1CCN(CC1)C(=O)C=1C=C(N)C=CC1 | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][cH:13][c:12]([C:10]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:20][CH2:19]2)=[O:11])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:18]2)[CH2:19][CH2:20]1 | CCOC(=O)C1CCN(C(=O)c2cccc([N+](=O)[O-])c2)CC1 | CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In like manner to the preparation of 3-(N-morpholinocarbonyl)aniline, 3-nitrobenzoylchloride and ethyl isonipecotate were reacted to prepare 1-[4-(ethoxycarbonyl)piperidinocarbonyl]-3-nitrobenzene which underwent hydrogenation to provide 3-[4-(ethoxycarbonyl)piperidinocarbonyl]aniline.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | Other | null | null | null | CCOC(=O)C1CCN(C(=O)c2cccc([N+](=O)[O-])c2)CC1>>CCOC(=O)C1CCN(C(=O)c2cccc(N)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36019a3ae0a64b5a87b2f10ee16f2a16 | Nc1cc(O)cc(O)c1.O=C(Cl)OCc1ccccc1>>O=C(Nc1cc(O)cc(O)c1)OCc1ccccc1 | NC=1C=C(C=C(C1)O)O.C(O)([O-])=O.[Na+].ClC(=O)OCC1=CC=CC=C1>>OC=1C=C(C=C(C1)O)NC(OCC1=CC=CC=C1)=O | [NH2:3][c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]([OH:10])[cH:11]1.Cl[C:2](=[O:1])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]([OH:10])[cH:11]1)[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | Nc1cc(O)cc(O)c1.O=C(Cl)OCc1ccccc1 | O=C(Nc1cc(O)cc(O)c1)OCc1ccccc1 | null | null | C1CCOC1.O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | HOUR | To a mixture of 5-aminobenzene-1,3-diol (0.60 g, 3.7 mmole) and sodium hydrogencarbonate (1.4 g, 16 mmole) in THF/water (15 mL, 1:1 v/v) was added dropwise benzyl chloroformate 1.6 mL, 11 mmole). After 3 h at rt, THF was removed under vacuum and the remaining aqueous layer was extracted with ethyl acetate. Purification... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1.O | null | 3 | Nc1cc(O)cc(O)c1.O=C(Cl)OCc1ccccc1>C1CCOC1.O>O=C(Nc1cc(O)cc(O)c1)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c54c369adfb4cf58c1e0f83a3b19adb | CCc1nc(C(=O)O)c2n1-c1cccc([N+](=O)[O-])c1OC2>>CCc1nc(C(=O)O)c2n1-c1cccc(N)c1OC2 | C(C)C1=NC(=C2COC3=C(N21)C=CC=C3[N+](=O)[O-])C(=O)O>>C(C)C1=NC(=C2COC3=C(N21)C=CC=C3N)C(=O)O | O=[N+:16]([O-])[c:15]1[cH:14][cH:13][cH:12][c:11]2[c:17]1[O:18][CH2:19][c:9]1[c:5]([C:6](=[O:7])[OH:8])[n:4][c:3]([CH2:2][CH3:1])[n:10]1-2>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6](=[O:7])[OH:8])[c:9]2[n:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]([NH2:16])[c:17]1[O:18][CH2:19]2 | CCc1nc(C(=O)O)c2n1-c1cccc([N+](=O)[O-])c1OC2 | CCc1nc(C(=O)O)c2n1-c1cccc(N)c1OC2 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)OCc1cncn1-2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#8:5]>>[#8:5]-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | Ethyl 6-Nitro-3-carboxy-4H-imidazo[5,1-c]-1,4-benzoxazine was reduced shaken in MeOH under 40 p.s.i. H2 with 20 weight percent of 10% Pd/C (Degussa) for 1 h then filtered and the solvent evaporated. The compound was purified directly by column chromatograph (EtOAc/hexane) to yield Ethyl 6-Amino-3-carboxy-4H-imidazo[5,1... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)OCc1cncn12 | Other | CO | null | null | CCc1nc(C(=O)O)c2n1-c1cccc([N+](=O)[O-])c1OC2>CO>CCc1nc(C(=O)O)c2n1-c1cccc(N)c1OC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27c4963bc17d426aa36be60b50506550 | CCOC(=O)CBr.O=[N+]([O-])c1cccc(O)c1>>CCOC(=O)COc1ccc([N+](=O)[O-])cc1 | [N+](=O)([O-])C=1C=C(C=CC1)O.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)OCC>>[N+](=O)([O-])C1=CC=C(OCC(=O)OCC)C=C1 | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][cH:15][c:11]([N+:12](=[O:13])[O-:14])[cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1 | CCOC(=O)CBr.O=[N+]([O-])c1cccc(O)c1 | CCOC(=O)COc1ccc([N+](=O)[O-])cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 664cb2c5aa93d9496524f5f298cd52563b53664e3db911a5c918b288f00ee895 | 7c6b97030dfbd5c28d157a269a4c38eb12a735419dab3d2d063f9d00b9333043 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c:13](-[OH;D1;+0:14]):[cH;D2;+0:15]:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:14]-[c:13]1:[c:12]:[cH;D2;+0:11]:[c;H0;D3;+0:9](-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:... | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC=C(OCC(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "[N+](=O)([O-])C1=CC=C(OCC(=O)OCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A dry reaction flask equipped with a reflux condenser, N2 inlet and a magnetic stirring bar was charged with 3-nitrophenol (76.45 g, 550 mmol), K2CO3 (76.45 g, 550 mmol) and dry acetone (500 mL) under N2 atmosphere. To this at room temperature was added ethyl bromoacetate (55.44 mL, 500 mmol) over a period of 15 min. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Nitro group.Aromatic alcohol | Ester.Ether.Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)C | null | null | CCOC(=O)CBr.O=[N+]([O-])c1cccc(O)c1>CC(=O)C>CCOC(=O)COc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca89c652e54f4d0283093d1a14cbefad | CCOC(=O)COc1ccc([N+](=O)[O-])cc1>>CCOC(=O)COc1ccc(N)cc1 | [N+](=O)([O-])C1=CC=C(OCC(=O)OCC)C=C1>>NC1=CC=C(OCC(=O)OCC)C=C1 | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:14][cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]1 | CCOC(=O)COc1ccc([N+](=O)[O-])cc1 | CCOC(=O)COc1ccc(N)cc1 | null | [Pd] | CCO | 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] | null | [] | null | null | null | null | A solution of ethyl 4-nitrophenoxyacetate (15 g) in EtOH (400 mL) was hydrogenated at 40 PSI for 40 minutes in the presence of 10% Pd/C (1.5 g, 10% by weight). After the filtration through a celite the solvent was removed under a reduced pressure to obtain ethyl 4-aminophenoxyacetate. 1H NMR (CDCl3): δ 6.77 (d, 2H, 8.1... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CCO | null | null | CCOC(=O)COc1ccc([N+](=O)[O-])cc1>[Pd].CCO>CCOC(=O)COc1ccc(N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a126ce362ce498ba2ed5afe4450f8d1 | CCOC(=O)COc1cccc([N+](=O)[O-])c1.CN>>CNC(=O)COc1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(OCC(=O)OCC)C=CC1.Cl.CN.C(C)(C)N(CC)C(C)C>>CNC(COC1=CC(=CC=C1)[N+](=O)[O-])=O | CCO[C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | CCOC(=O)COc1cccc([N+](=O)[O-])c1.CN | CNC(=O)COc1cccc([N+](=O)[O-])c1 | null | null | O.CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C;D1;H3:5] | 95 | [{"value": 95.0, "product": "CNC(COC1=CC(=CC=C1)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 6 | HOUR | A mixture of ethyl 3-nitrophenoxyacetate (9.12 g, 40 mmol), methylamine hydrochloride (26.8 g, 400 mmol) and diisopropylethylamine (35.5 mL, 200 mL) in MeOH (100 mL) was stirred in a pressure vial at 90° C. for 6 h. The reaction was cooled to room temperature, diluted with water (1 liter), the solid formed was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O.CO | 90 | 6 | CCOC(=O)COc1cccc([N+](=O)[O-])c1.CN>O.CO>CNC(=O)COc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cebac8d5e40b4ab58170713af975d28e | O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>>COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 | N1=CC=CC=C1.CN(C)C=O.[N+](=O)([O-])C=1C=CC2=C(C=C(O2)C(=O)O)C1.C(=O)(C(=O)Cl)Cl>>COC(=O)C=1OC2=C(C1)C=C(C=C2)[N+](=O)[O-] | [OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[o:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[o:16]1 | O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1 | COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 | null | null | C(Cl)Cl.CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccc2occc2c1 | [#8;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[#8;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;D1;H3:6] | null | [] | 0 | CELSIUS | 1 | HOUR | To a suspension of 5-nitro-2-benzofurancarboxylic acid (5 g, 24.15 mmol) in CH2Cl2 (250 mL) at 0° C. was added DMF (0.100 mL) followed by (COCl)2 (2M in CH2Cl2, 36.23 mL, 72.46 mL) over a period of 10 min. The reaction was stirred at 0° C. for 1 h and then at room temperature for 30 min. The reaction solvent was remove... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2occc2c1 | Other | C(Cl)Cl.CO | 0 | 1 | O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>C(Cl)Cl.CO>COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-568a8ab47a9641218cc40e5c5d890b76 | CCOC(=O)C(C)(C)Br.O=[N+]([O-])c1cccc(O)c1>>CCOC(=O)C(C)(C)Oc1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC1)O.BrC(C(=O)OCC)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(=O)(O)[O-].[Na+]>>CC(C(=O)OCC)(C)OC1=CC(=CC=C1)[N+](=O)[O-] | Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8].[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | CCOC(=O)C(C)(C)Br.O=[N+]([O-])c1cccc(O)c1 | CCOC(=O)C(C)(C)Oc1cccc([N+](=O)[O-])c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 657b1e065fabda84e4d6cc80f4d94ce754af0792c9117981e41887a4384f6981 | 2495a256265ef36132d409a6a3e2bd04c3acda5f236d910f184b0a36a846defe | c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | 70 | CELSIUS | null | null | A mixture of 3-nitrophenol (0.50 g, 3.6 mmole), ethyl bromodimethylacetate (0.64 g, 3.3 mmole), K2CO3 (1.3 g, 9.4 mmole), potassium iodide (catalytic) in absolute ethanol (8 mL) was heated at 70° C. for 18 h. The reaction mixture was cooled, poured into a saturated solution of NaHCO3, and extracted with dichloromethane... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)O | 70 | null | CCOC(=O)C(C)(C)Br.O=[N+]([O-])c1cccc(O)c1>C(C)O>CCOC(=O)C(C)(C)Oc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89890b89152d42efb4769650628a1fa6 | ClCc1nc(-c2ccccc2)no1.O=[N+]([O-])c1ccc(O)cc1>>O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)O.ClCC1=NC(=NO1)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1 | Cl[CH2:9][c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][o:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:21][cH:22]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][o:20]2)[cH:21][cH:22]1 | ClCc1nc(-c2ccccc2)no1.O=[N+]([O-])c1ccc(O)cc1 | O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2nc(-c3ccccc3)no2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[#8;a:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[#8;a:6]:1):[c:10] | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Nitrophenol (0.36 g, 2.56 mmole), 5-(chloromethyl)-3-phenyl-1,2,4-oxadiazole (0.5 g, 2.56 mmole) and anhydrous K2CO3 (0.39 g, 2.82 mmole) were dissolved in anhydrous acetone (20 mL) and heated to reflux for 12 h. Reaction mixture was cooled and the solvent removed under vacuum. The crude solid formed was collected by... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ncon1.c1ccccc1 | HCl | CC(=O)C | null | null | ClCc1nc(-c2ccccc2)no1.O=[N+]([O-])c1ccc(O)cc1>CC(=O)C>O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c94a7eabd2c49d08e80c3d49d7fbb30 | O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1>>Nc1ccc(OCc2nc(-c3ccccc3)no2)cc1 | [N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1.S(=O)([O-])S(=O)[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>>NC1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][o:18]2)[cH:19][cH:20]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][o:18]2)[cH:19][cH:20]1 | O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1 | Nc1ccc(OCc2nc(-c3ccccc3)no2)cc1 | null | null | CO.C(Cl)Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCc2nc(-c3ccccc3)no2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 51.2 | [{"value": 51.0, "product": "NC1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.2, "product": "NC1=CC=C(OCC2=NC(=NO2)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 5-[(4-nitrophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole (0.5 g, 1.68 mmole) was dissolved in methanol:methylenechloride (1:1) (120 mL). Aqueous solution of (15 mL) sodium hydrosulfite (0.88 g, 5.05 mmole) and K2CO3 (0.70 g, 5.06 mmole) was added dropwise under nitrogen for 10 min. The contents were allowed to stir at ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ncon1.c1ccccc1 | Other | CO.C(Cl)Cl | null | null | O=[N+]([O-])c1ccc(OCc2nc(-c3ccccc3)no2)cc1>CO.C(Cl)Cl>Nc1ccc(OCc2nc(-c3ccccc3)no2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-609dc61e4792466db2fac5583896ffa6 | CCN(CC)CC.CCN=C=NCCCN(C)C.O=C(O)COc1ccc([N+](=O)[O-])cc1>>Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1 | [N+](=O)([O-])C1=CC=C(OCC(=O)O)C=C1.Cl.C(C)N(CC)CC.CCN=C=NCCCN(C)C.Cl.C(C)(C)N(CC)C(C)C>>[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C)C=C1 | CCN(CC)C[CH3:1].CC[N:3]=[C:2]=[N:17]CCCN(C)C.O=[C:5]([OH:4])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[n:17]1 | CCN(CC)CC.CCN=C=NCCCN(C)C.O=C(O)COc1ccc([N+](=O)[O-])cc1 | Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 38dedeaf21b1f6bbd5763e3f2c3b55dcd539759f66ff034dbc5202f9fc53b5ea | 729c708d21fd4decabd11b54943b602f9c848df18bdbfa5dc44add08714f2cc2 | c1ccc(OCc2ncno2)cc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].C-C-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[N;H0;D2;+0:4]-C-C-C-N(-C)-C.O=[C;H0;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[#8:8]>>[#8:8]-[C:7]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[c;H0;D3;+0:3](-[CH3;D1;+0:1]):[n;H0;D2;+0:2]:[o;H0;D2;+0:6]:1 | 60.4 | [{"value": 60.0, "product": "[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "[N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-nitrophenoxy acetic acid (2.25 g, 11.4 mmole), acetamideoxime, triethylamine hydrochloride (3.85 g, 27.62 mmole), EDCI.HCl (4.37 g, 22.79 mmole) and diisopropylethylamine (7.42 g, 57.40 mmole) in anhydrous THF (250 ml) was refluxed for 18 h. The unhomogenous brown colored reaction mixture was quenched wi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine.Tertiary amine | null | null | c1ncon1 | c1ncon1.c1ccccc1 | HO- | C1CCOC1 | null | null | CCN(CC)CC.CCN=C=NCCCN(C)C.O=C(O)COc1ccc([N+](=O)[O-])cc1>C1CCOC1>Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-347eda565b6444378d4c476ca64f0801 | Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1>>Cc1noc(COc2ccc(N)cc2)n1 | [N+](=O)([O-])C1=CC=C(OCC2=NC(=NO2)C)C=C1.S(=O)([O-])S(=O)[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>>NC1=CC=C(OCC2=NC(=NO2)C)C=C1 | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][c:5]2[o:4][n:3][c:2]([CH3:1])[n:15]2)[cH:14][cH:13]1>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[n:15]1 | Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1 | Cc1noc(COc2ccc(N)cc2)n1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCc2ncno2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In like manner to the preparation of 5-[(4-aminophenoxy)methyl]-3-phenyl-1,2,4-oxadiazole, 5-(4-nitrophenoxymethyl)-3-methyl-1,2,4-oxadiazole was reacted with aqueous solution of sodium hydrosulfite and K2CO3 to prepare 5-[(4-aminophenox)ymethyl]-3-methyl-1,2,4-oxadiazole. 1H NMR (CDCl3): δ 6.82 (d, 2H, J=8.8 Hz), 6.63... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncon1.c1ccccc1 | Other | null | null | null | Cc1noc(COc2ccc([N+](=O)[O-])cc2)n1>>Cc1noc(COc2ccc(N)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfce5dd4e1cf497283f9edf57a9691a2 | NNC(=O)c1cccc(Cl)c1.O=C(Cl)c1cccc([N+](=O)[O-])c1>>O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1 | ClC=1C=C(C(=O)NN)C=CC1.N1=CC=CC=C1.[N+](=O)([O-])C=1C=C(C(=O)Cl)C=CC1>>ClC=1C=C(C(=O)NNC(=O)C2=CC(=CC=C2)[N+](=O)[O-])C=CC1 | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1.Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1 | NNC(=O)c1cccc(Cl)c1.O=C(Cl)c1cccc([N+](=O)[O-])c1 | O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C(NNC(=O)c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[O;D1;H0:9]=[C:8](-[c:10])-[#7:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of 3-chlorobenzohydrazide (1 equivalent) and pyridine (2 equivalents) in CH2Cl2 at 0° C. was added a CH2Cl2 solution of 3-nitrobenzoyl chloride (1 equivalents) and stirred at 0° C. for 1 h and then at room temperature for overnight. The resulting solution was concentrated and diluted with water, basified ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | NNC(=O)c1cccc(Cl)c1.O=C(Cl)c1cccc([N+](=O)[O-])c1>C(Cl)Cl>O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27e08cdeb49d49e19db3a70c77cc2346 | O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1>>O=[N+]([O-])c1cccc(-c2nnc(-c3cccc(Cl)c3)o2)c1 | ClC=1C=C(C(=O)NNC(=O)C2=CC(=CC=C2)[N+](=O)[O-])C=CC1>>ClC=1C=C(C=CC1)C=1OC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-] | O=[C:9]([c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21]1)[NH:10][NH:11][C:12]([c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1)=[O:20]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]3)[o:20]2)[cH:21]1 | O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1 | O=[N+]([O-])c1cccc(-c2nnc(-c3cccc(Cl)c3)o2)c1 | null | null | O=P(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(-c2nnc(-c3ccccc3)o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[o;H0;D2;+0:5]:1)... | null | [] | 90 | CELSIUS | 24 | HOUR | A suspension of N′1-(3-chlorobenzoyl)-3-nitrobenzene-1-carbohydrazide (0.321 g) in POCl3 (3 mL) was stirred at 90° C. for 24 h. The resulting clear solution was quenched with ice-water, solid obtained was filtered washed with water, dried and analyzed to give [2-(3-chlorophenyl)-1,3,4-oxadiazol-5-yl]-3-nitrobenzene. 1H... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1ccccc1.c1nnco1.c1ccccc1 | HO- | O=P(Cl)(Cl)Cl | 90 | 24 | O=C(NNC(=O)c1cccc([N+](=O)[O-])c1)c1cccc(Cl)c1>O=P(Cl)(Cl)Cl>O=[N+]([O-])c1cccc(-c2nnc(-c3cccc(Cl)c3)o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7c9d603decf4cf58d894b1d59c4f3a4 | CO.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>>COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 | C(=O)(O)C=1OC2=C(C1)C=C(C=C2)[N+](=O)[O-].OS(=O)(=O)O.CO>>COC(=O)C=1OC2=C(C1)C=C(C=C2)[N+](=O)[O-] | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[o:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[o:16]1 | CO.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1 | COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2occc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | 60 | CELSIUS | null | null | A mixture of 2-carboxy-5-nitrobenzofuran (2.0 g), MeOH (10 mL) and Concentrated H2SO4 (2.1 mL) was heated in a sealed tube at 60° C. for 3 h. Upon cooling to the room temperature it was quenched with ice-water and carefully basified with addition of NaHCO3. The solid obtained was filtered, washed with water, dried and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2occc2c1 | HO- | null | 60 | null | CO.O=C(O)c1cc2cc([N+](=O)[O-])ccc2o1>>COC(=O)c1cc2cc([N+](=O)[O-])ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c961b35f5934314a9f268ca10233648 | CCOC(=O)C(C)(Br)C(=O)OCC.O=[N+]([O-])c1cccc(O)c1>>CCOC(=O)C(C)(Oc1cccc([N+](=O)[O-])c1)C(=O)OCC | BrC(C(=O)OCC)(C(=O)OCC)C.[F-].[K+].[N+](=O)([O-])C=1C=C(C=CC1)O>>CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-] | Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[C:18](=[O:19])[O:20][CH2:21][CH3:22].[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([O:8][c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1)[C:18](=[O:19])[O:20][CH2:21][CH3:22] | CCOC(=O)C(C)(Br)C(=O)OCC.O=[N+]([O-])c1cccc(O)c1 | CCOC(=O)C(C)(Oc1cccc([N+](=O)[O-])c1)C(=O)OCC | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a978d72dbce2e1c9544ed52f568b218c48df2a275de5def4b5c34dfe9d585cf2 | fca6f127b31377df5b22e7de2665721fdb7e59654f5d2c438f0e61c7b1dfe1e9 | c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 80 | [{"value": 80.0, "product": "CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Diethyl 2-bromo-2-methylmalonate (1.0 g, 3.95 mmole) was added to a stirred suspension of potassium fluoride (0.57 g, 9.8 mmole) in dry DMF (5 mL). After stirring for 20 min at room temperature, 3-nitrophenol (0.55 g, 3.95 mmole) was added. The resulting mixture was stirred at 60° C. for 6 h, cooled to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Ester.Aromatic alcohol | Ester.Ester.Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | null | 0.333333 | CCOC(=O)C(C)(Br)C(=O)OCC.O=[N+]([O-])c1cccc(O)c1>O.CN(C)C=O>CCOC(=O)C(C)(Oc1cccc([N+](=O)[O-])c1)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-587fec88427c4634a2c488307af766bb | COC(=O)c1ccc(CCl)o1.O=[N+]([O-])c1cccc(O)c1>>COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1 | [N+](=O)([O-])C=1C=C(C=CC1)O.ClCC1=CC=C(O1)C(=O)OC.C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C1=CC=C(OCC=2C=C(OC2)C(=O)OC)C=C1 | Cl[CH2:8][c:19]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:20]1.[OH:9][c:10]1[cH:11][cH:12][cH:17][c:13]([N+:14](=[O:15])[O-:16])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[cH:19][o:20]1 | COC(=O)c1ccc(CCl)o1.O=[N+]([O-])c1cccc(O)c1 | COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1 | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4f45ae9ef548a2289c3a3fb1f214a1d6c393ee242a0a18fe1d74d8a18911210b | 97f387adea3400d62dbfc57ddb96ecb153250bfe87f2299caf6788e9ed783cc6 | c1ccc(OCc2ccoc2)cc1 | Cl-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1.[O;-;D1;H0:10]-[#7;+:11](=[O;D1;H0:12])-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[c:16]:[c:17](-[OH;D1;+0:18]):[cH;D2;+0:19]:1>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:3]:[cH;D2;+0:2]:[c;H0;D3;+0:9](-[CH2;D2;+0:1]-[O;H... | 90.8 | [{"value": 90.0, "product": "[N+](=O)([O-])C1=CC=C(OCC=2C=C(OC2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "[N+](=O)([O-])C1=CC=C(OCC=2C=C(OC2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Nitrophenol (1.0 g, 7.19 mmole), methyl 5-(chloromethyl)-2-furoate (1.38 g, 7.90 mmole) and anhydrous K2CO3 (1.19 g, 8.60 mmole) in acetone (30 mL) were refluxed for 8 h. The reaction mixture was cooled and diluted with water. The resultant white solid was filtered, washed with water and air dried overnight to give 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitro group.Aromatic alcohol | Ether.Nitro group | c1ccoc1.c1ccccc1 | c1ccoc1.c1ccccc1 | c1ccoc1.c1ccccc1 | HCl | O.CC(=O)C | null | null | COC(=O)c1ccc(CCl)o1.O=[N+]([O-])c1cccc(O)c1>O.CC(=O)C>COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a92ac7f28724a3da16cca0f1b5601dd | COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1>>COC(=O)c1cc(COc2ccc(N)cc2)co1 | CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-].[N+](=O)([O-])C1=CC=C(OCC=2C=C(OC2)C(=O)OC)C=C1>>NC1=CC=C(OCC=2C=C(OC2)C(=O)OC)C=C1 | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:18][cH:17]2)[cH:16][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]2)[cH:17][o:18]1 | COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1 | COC(=O)c1cc(COc2ccc(N)cc2)co1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCc2ccoc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, 4-(4-nitrophenoxymethyl)-2-methoxycarbonyl-furan was reduced to provide 4-(4-aminophenoxymethyl)-2-methoxycarbonyl-furan. 1H NMR (CDCl3): δ 7.15 (d, 1H, J=3.5 Hz), 7.05 (t, 1H, J=8.2 Hz), 6.50 (d, 1H, J=3.5 Hz), 6.37-6.27 (m, 3H), 5.01 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccoc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(COc2ccc([N+](=O)[O-])cc2)co1>>COC(=O)c1cc(COc2ccc(N)cc2)co1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20a3d9d8ba2b46a4b61ef490a9cd9f4f | COC(=O)c1ccc(Cn2ncc3ccc([N+](=O)[O-])cc32)c(OC)c1>>COC(=O)c1ccc(Cn2ncc3ccc(N)cc32)cc1 | CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-].COC=1C=C(C(=O)OC)C=CC1CN1N=CC2=CC=C(C=C12)[N+](=O)[O-]>>NC1=CC=C2C=NN(C2=C1)CC1=CC=C(C(=O)OC)C=C1 | CO[c:20]1[c:8]([CH2:9][n:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([N+:17](=O)[O-])[cH:18][c:19]23)[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[n:11][cH:12][c:13]3[cH:14][cH:15][c:16]([NH2:17])[cH:18][c:19]23)[cH:20][cH:21]1 | COC(=O)c1ccc(Cn2ncc3ccc([N+](=O)[O-])cc32)c(OC)c1 | COC(=O)c1ccc(Cn2ncc3ccc(N)cc32)cc1 | null | null | null | Reduction | OtherReaction | aef5dc601739ebd32e43f0aeb9bd99f2c2dbb5184e88a715f83a4f6e66224812 | cf3c5d646c268a72dcb4539d88108a61d0ba75093223853e2389d3882648e1de | c1ccc(Cn2ncc3ccccc32)cc1 | C-O-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[C:8]-[#7;a:9]:[c:10]:[c:11]:[c:12](-[N+;H0;D3:13](=O)-[O-]):[c:14]):[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[cH;D2;+0:1]:[c:7](-[C:8]-[#7;a:9]:[c:10]:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, methyl 3-methoxy-4-[(6-nitroindazol-1-yl)methyl]benzoate was reduced to provide methyl 4-[(6-aminoindazol-1-yl)methyl]benzoate. 1H NMR (CDCl3): δ 7.88 (s, 1H), 7.53 (d, 1H, J=8.8 Hz), 7.51 (d, 1H, J=8.8 Hz), 7.50 (d, 1H, J=1.7 Hz), 6.67 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2cn[nH]c2c1 | Other | null | null | null | COC(=O)c1ccc(Cn2ncc3ccc([N+](=O)[O-])cc32)c(OC)c1>>COC(=O)c1ccc(Cn2ncc3ccc(N)cc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e276eddb5c5a408ea4f9beccd79cceea | COC(=O)c1ccc(Cn2cc3ccc([N+](=O)[O-])cc3n2)c(OC)c1>>COC(=O)c1ccc(Cn2cc3ccc(N)cc3n2)cc1 | CC(C(=O)OCC)(C(=O)OCC)OC1=CC(=CC=C1)[N+](=O)[O-].COC=1C=C(C(=O)OC)C=CC1CN1N=C2C=C(C=CC2=C1)[N+](=O)[O-]>>NC=1C=CC2=CN(N=C2C1)CC1=CC=C(C(=O)OC)C=C1 | CO[c:20]1[c:8]([CH2:9][n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([N+:16](=O)[O-])[cH:17][c:18]3[n:19]2)[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([NH2:16])[cH:17][c:18]3[n:19]2)[cH:20][cH:21]1 | COC(=O)c1ccc(Cn2cc3ccc([N+](=O)[O-])cc3n2)c(OC)c1 | COC(=O)c1ccc(Cn2cc3ccc(N)cc3n2)cc1 | null | null | null | Reduction | OtherReaction | aef5dc601739ebd32e43f0aeb9bd99f2c2dbb5184e88a715f83a4f6e66224812 | cf3c5d646c268a72dcb4539d88108a61d0ba75093223853e2389d3882648e1de | c1ccc(Cn2cc3ccccc3n2)cc1 | C-O-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[C:8]):[c:9].O=[N+;H0;D3:10](-[O-])-[c:11](:[c:12]):[c:13]:[c:14]:[#7;a:15]>>[#7;a:15]:[c:14]:[c:13]:[c:11](-[NH2;D1;+0:10]):[c:12].[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[cH;D2;+0:1]:[c:7](-[C:8]):[c:9] | null | [] | null | null | null | null | In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, methyl 3-methoxy-4-[(6-nitroindazol-2-yl)methyl]benzoate was reduced to provide methyl 4-[(6-aminoindazol-2-yl)methyl]benzoate. 1H NMR (CDCl3): δ 7.78 (s, 1H), 7.56-7.53 (m, 2H), 7.43 (d, 1H, J=8.8 Hz), 6.98 (d, 1H, J=8.2 Hz), 6.81 (app s, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c[nH]nc2c1 | Other | null | null | null | COC(=O)c1ccc(Cn2cc3ccc([N+](=O)[O-])cc3n2)c(OC)c1>>COC(=O)c1ccc(Cn2cc3ccc(N)cc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfc3f15dd35742c8b9a7f4d9e75a5814 | CCOc1ccc(N)cc1.Clc1ccnc(Cl)n1>>CCOc1ccc(Nc2ccnc(Nc3ccc(OCC)cc3)n2)cc1 | Cl.ClC1=NC=CC(=N1)Cl.C(C)OC1=CC=C(N)C=C1>>C(C)OC1=CC=C(C=C1)NC1=NC=CC(=N1)NC1=CC=C(C=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:25][cH:26]1.Cl[c:9]1[cH:10][cH:11][n:12][c:13](Cl)[n:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][CH2:20][CH3:21])[cH:22][cH:23]3)[n:24]2)[cH:25][cH:26]1 | CCOc1ccc(N)cc1.Clc1ccnc(Cl)n1 | CCOc1ccc(Nc2ccnc(Nc3ccc(OCC)cc3)n2)cc1 | null | null | O.CCO | Aromatic Heterocycle Formation | OtherReaction | 62f223343fbca7566af616417c883149b0507fc398dcae296734119b0aa5bf8e | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-Cl):[#7;a:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:11]-[#7:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:6]:1 | null | [] | 75 | CELSIUS | null | null | To a solution of 2,4-dichloropyrimidine (0.015 g, 0.1 mmol) in EtOH (1 mL) was added 4-ethoxyaniline (0.034 g, 0.025 mmol) and heated in a sealed tube at 70-80° C. for 24 h. Upon cooling the reaction was diluted with H2O (10 mL), acidified with 2N HCl, the solid obtained was filtered, washed with H2O and dried to give ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CCO | 75 | null | CCOc1ccc(N)cc1.Clc1ccnc(Cl)n1>O.CCO>CCOc1ccc(Nc2ccnc(Nc3ccc(OCC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62ab4600963044e7a7b5049db70d2242 | Fc1cnc(Cl)nc1Cl.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(C=CC1)O.Cl>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13](Cl)[n:14]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][cH:18][c:19]([OH:20])[cH:21]3)[n:22]2)[cH:23]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 50b6c6d1c426cfb366c3e2794bcb22c935f693104ff044ea8802bff159e6151c | 21ac61801f680a0fd4713aa79572457ec8c95552d1bd22e84dee389ea1fa0604 | 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:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | A mixture of 2,4-dichloro-5-fluoropyrimidine (0.0167 g, 0.1 mmol) and 3-aminophenol (0.033 g, 0.3 mmol) in MeOH:H2O (1.8:0.2 mL; v/v) was shaken in a sealed tube at 100° C. for 24 h (or 80 oC for 3 days), cooled to room temperature, diluted with water (15 mL), acidified with 2N HCl (pH>2). Upon saturation with sodium c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic alcohol.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(O)c1>O.CO>Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-942bf97fd474447aabbeb2dbf0c49ace | COc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)F.COC1=CC=C(N)C=C1>>COC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:24][cH:25]1.Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13](Cl)[n:14]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]([O:19][CH3:20])[cH:21][cH:22]3)[n:23]2)[cH:24][cH:25]1 | COc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 62f223343fbca7566af616417c883149b0507fc398dcae296734119b0aa5bf8e | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | 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:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-methoxyaniline were reacted to yield N2,N4-bis(4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.67 (d, 1H, J=4.8 Hz), 7.43 (d, 2H, J=9.3 Hz), 7.67 (d, 2H, J=8.7 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-438dd5f139864c009a8612199626a758 | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)c(F)c1>>Fc1cc(Nc2ncc(F)c(Nc3ccc(C(F)(F)F)c(F)c3)n2)ccc1C(F)(F)F | ClC1=NC=C(C(=N1)Cl)F.FC=1C=C(N)C=CC1C(F)(F)F>>FC=1C=C(C=CC1C(F)(F)F)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(F)(F)F)F)F | Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11](Cl)[n:12]1.[F:1][c:2]1[cH:3][c:4]([NH2:5])[cH:25][cH:26][c:27]1[C:28]([F:18])([F:19])[F:31]>>[F: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]([C:17]([F:18])([F:19])[F:20])[c:21]([F:22])[cH:23]3)[n:24]2)[cH:25][cH:26][c:27]1[C:28]... | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)c(F)c1 | Fc1cc(Nc2ncc(F)c(Nc3ccc(C(F)(F)F)c(F)c3)n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a5e7f2831151a784456ee89cd477aaec4df63fd3cc0e5fd43aa9fb10b8e9d13d | 3cbb665051b602f351ed7c6fc0d3120bc5dc730b9c8344f54bbe2677906786ec | 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;D1;H0:8]-[C;H0;D4;+0:9](-[F;H0;D1;+0:10])(-[F;H0;D1;+0:11])-[c:12]1:[c:13]:[c:14]:[c:15](-[NH2;D1;+0:16]):[c:17]:[c:18]:1>>[F;D1;H0:19]-[C:20](-[F;H0;D1;+0:10])(-[F;H0;D1;+0:11])-[c:21].[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-fluoro-4-trifluoromethylaniline were reacted to yield N2,N4-bis(3-fluoro-4-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.01 (d, 1H, J=3 Hz), 7.77 (m, 3H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Primary amine | Trifluoro group.Trifluoro group.Aromatic halide.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(C(F)(F)F)c(F)c1>>Fc1cc(Nc2ncc(F)c(Nc3ccc(C(F)(F)F)c(F)c3)n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92410daaba8442308314b1e578082cb5 | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1>>Fc1cnc(Nc2cccc(OC(F)(F)F)c2)nc1Nc1cccc(OC(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.FC(OC=1C=C(N)C=CC1)(F)F>>FC(OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OC(F)(F)F)F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:19](Cl)[n:18]1.[cH:8]1[cH:9][cH:10][c:11]([O:12][C:13]([F:14])([F:15])[F:28])[cH:17][c:21]1[NH2:20]>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C:13]([F:14])([F:15])[F:16])[cH:17]2)[n:18][c:19]1[NH:20][c:21]1[cH:22][cH:23][cH:24][c:25]([O:26][C:27]([F:28])... | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1 | Fc1cnc(Nc2cccc(OC(F)(F)F)c2)nc1Nc1cccc(OC(F)(F)F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | aeb2fb23b1babea52692a078b92a706eea6f1320c3781c5bf99ca7997ca0fda3 | f26eb2c2d78d37d2efd07d3d0a8535b3c194cacfe394d7d6eeb3cb1662db753f | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[F;D1;H0:8]-[C;H0;D4;+0:9](-[F;D1;H0:10])(-[F;H0;D1;+0:11])-[#8:12]-[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17](-[NH2;D1;+0:18]):[cH;D2;+0:19]:1>>[F;D1;H0:8]-[C;H0;D4;+0:9](-[F;D1;H0:10])(-[F;D1;H0:20])-[#8:12]-[c:13]1:[c:14]:[c:... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-trifluoromethoxyaniline were reacted to yield N2,N4-bis(3-trifluoromethoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.03 (bd, 1H), 7.62 (bs, 2H), 7.48 (bd, 1H), 7.39 (t, ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Ether.Primary amine | Trifluoro group.Trifluoro group.Ether.Ether.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(OC(F)(F)F)c1>>Fc1cnc(Nc2cccc(OC(F)(F)F)c2)nc1Nc1cccc(OC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69371bed02b34a38bf132ecf8ad7ed2f | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1>>Fc1cnc(Nc2ccc(Cl)c(C(F)(F)F)c2)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.ClC1=C(C=C(N)C=C1)C(F)(F)F>>ClC1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)Cl)C(F)(F)F)F)C(F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:7]([Cl:11])[n:6]1.[c:12]1([C:13]([F:14])([F:16])[F:28])[cH:17][c:21]([NH2:20])[cH:22][cH:26][c:24]1[Cl:25]>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]2)[n:18][c:19]1[NH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[c:26]([C:... | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1 | Fc1cnc(Nc2ccc(Cl)c(C(F)(F)F)c2)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 96d7c1880dafbf1c8f5055625b891411bc57c87793ff3d4abdef8a238f4734ff | 807c9631cee0ce62f3ca13efaa5b2a56fc05969e15670b9729db6ac0dbb8917c | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[Cl;D1;H0:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:[c;H0;D3;+0:16]:1-[C;H0;D4;+0:17](-[F;D1;H0:18])(-[F;D1;H0:19])-[F;H0;D1;+0:20]>>[Cl;D1;H0:9]-[c;H0;D3... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-chloro-3-trifluoromethylaniline were reacted to yield N2,N4-bis(4-chloro-3-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.05 (bs, 1H), 7.89 (bd, 1H), 7.77 (dd... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Trifluoro group.Trifluoro group.Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)c(C(F)(F)F)c1>>Fc1cnc(Nc2ccc(Cl)c(C(F)(F)F)c2)nc1Nc1ccc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98f250f36bc24f1896cfca119dc3efb1 | CCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCC)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C)OC=1C=C(N)C=CC1>>C(C)OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OCC)F | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:27]1.Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15](Cl)[n:16]1>>[CH3:1][CH2:2][O: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][c:21]([O:22][CH2:23][CH3:24])[cH:25]3)[n:26]2)[cH:27]1 | CCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl | CCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCC)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 62f223343fbca7566af616417c883149b0507fc398dcae296734119b0aa5bf8e | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | 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.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:6]:1-[NH;D2;+0:7]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-ethoxyaniline were reacted to yield N2,N4-bis(3-ethoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.96 (1H, d, J=4.8 Hz), 7.22 (m, 6H), 7.07 (t, 1H, J=1.8 Hz), 6.95 (dt, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cca3e56ecb674e63a41603ff14eeb288 | COc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(O)c3)n2)cc1O | ClC1=NC=C(C(=N1)Cl)F.OC=1C=C(N)C=CC1OC>>OC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)O)F | [CH3:1][O:2][c:3]1[c:18]([OH:19])[cH:21][c:6]([NH2:7])[cH:4][cH:26]1.Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13](Cl)[n:14]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]([O:19][CH3:20])[c:21]([OH:22])[cH:23]3)[n:24]2)[cH:25][c:26]1[OH:27] | COc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(O)c3)n2)cc1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 588f7bbaa5a94cf89f23f36080e9a10761c6eb13b7c1dae6ffd026e7982bd52b | ca2fce1788b95ea90170147e4c594fb9fe7d97d178f6231d591073ba9e3702da | 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].[C;D1;H3:8]-[#8:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[C;D1;H3:8]-[#8:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:12]:[c:18]:[c;H0;D3;+0:13](-[NH;D2;+0:14]... | null | [] | null | null | null | null | In like manner to N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-hydroxy-4-methoxylaniline were reacted to yield N2,N4-bis(3-hydroxy-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.82 (d, 1H J=4 Hz), 7.18 (m, 2H), 6.95 (m, 2H), 6.83 (m, 2H) 3.93 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Aromatic alcohol.Primary amine | Ether.Ether.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(O)c3)n2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c425d9ada8740fc9aa210e1e4d4ecf0 | CCOC(=O)Nc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>CCOC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OCC)c(O)c3)n2)cc1O | ClC1=NC=C(C(=N1)Cl)F.C(C)OC(=O)NC1=C(C=C(N)C=C1)O>>C(C)OC(=O)NC1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)NC(=O)OCC)O)F)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:33][c:34]1[OH:35].Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17](Cl)[n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH: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][c:19]3[cH:20][cH:21][c:22]([NH:23][C:24](=[O:25])[O:... | CCOC(=O)Nc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl | CCOC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OCC)c(O)c3)n2)cc1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d4b07d99e072563d97ea823d536e574e8349dbde5677e043465d08b95f4f16ab | 9d48df8f89e67794a5df78af454bcdf1be6eb9cf995a925d32fc729d1c9f4a2d | 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.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:6]:1-[NH;D2;+0:7]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-ethoxycarbonylamino-3-hydroxyaniline were reacted to yield N2,N4-bis(4-ethoxycarbonylamino-3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.86 (d, 1H J=4 Hz), 7.67 (m, 2H), 7.20 (dd, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Carbamic ester.Ether.Aromatic alcohol.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CCOC(=O)Nc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>CCOC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OCC)c(O)c3)n2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c853bf4c6983424990e90f80c2d938e9 | Cc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(O)c3)n2)cc1O | ClC1=NC=C(C(=N1)Cl)F.OC=1C=C(N)C=CC1C>>OC=1C=C(C=CC1C)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C)O)F | [cH:3]1[cH:4][c:5]([NH2:6])[cH:21][c:19]([OH:20])[c:17]1[CH3:18].Cl[c:1]1[n:8][cH:9][c:10]([F:11])[c:23](Cl)[n:13]1>>[CH3:1][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]([CH3:18])[c:19]([OH:20])[cH:21]3)[n:22]2)[cH:23][c:24]1[OH:25] | Cc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl | Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(O)c3)n2)cc1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6429378113b0579ba4d379b0179a67c7e51d853417c515a151d9c3829a0aef33 | d1646659140e64690c3d3151bde8a33779aa9c9df53cbbffc3d43a81348dfedd | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[c;H0;D3;+0:4](-[F;D1;H0:5]):[c:6]:[n;H0;D2;+0:7]:1.[C;D1;H3:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c;H0;D3;+0:12](-[NH2;D1;+0:13]):[cH;D2;+0:14]:[c:15]:1-[O;D1;H1:16]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c:17]:[c:18]:[c:19](-[NH;D2;+0:2]-[c:20]2:[#7;a:21]:[c:22](-[NH;D2... | null | [] | null | null | null | null | In like manner to N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-hydroxy-4-methylaniline were reacted to yield N2,N4-bis(−3-hydroxy-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.83 (d, 1H J=4 Hz), 7.11 (m, 4H), 6.81 (m, 2H), 2.19 (m, 6H); LCMS: ret... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic alcohol.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Cc1ccc(N)cc1O.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(O)c3)n2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de07cd2985864c33833a4d7ee0f5bb66 | COc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>COc1cccc(Nc2ncc(F)c(Nc3cccc(OC)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.COC=1C=C(N)C=CC1>>COC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:25]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14](Cl)[n:15]1>>[CH3:1][O:2][c:3]1[cH:4][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]([O:21][CH3:22])[cH:23]3)[n:24]2)[cH:25]1 | COc1cccc(N)c1.Fc1cnc(Cl)nc1Cl | COc1cccc(Nc2ncc(F)c(Nc3cccc(OC)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 62f223343fbca7566af616417c883149b0507fc398dcae296734119b0aa5bf8e | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | 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:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-methoxyaniline were reacted to yield N2,N4-bis(3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.96 (d, 1H, J=5.4 Hz), 7.24 (m, 6H), 7.06 (t, 1H, J=2.4 Hz), 7.00 (dt, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>COc1cccc(Nc2ncc(F)c(Nc3cccc(OC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c9d0c7f36f541d8a49d2c1b160b6eea | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)Cl)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)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:18](Cl)[n:6]1.[CH2:7]1[O:13][c:23]2[cH:22][cH:21][c:20]([NH2:19])[cH:25][c:24]2[O:26][CH2:27]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[O:13][CH2:14][CH2:15][O:16]3)[n:17][c:18]1[NH:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[O:26][CH2:27][CH2:28... | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2 | Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e0e9888bfcd9a9766d417e66337615a3b5c05c206e944a8ebf0dc5096017b90a | 803f8514cb09365110cfadee6d865ca3b804582a022196c598b58ac3ea09b716 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3c(c2)OCCO3)n1 | 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:9]1:[c:10]:[c:11]:[c;H0;D3;+0:12]2:[c:13](:[c:14]:1)-[#8:15]-[CH2;D2;+0:16]-[CH2;D2;+0:17]-[O;H0;D2;+0:18]-2>>[C:19]-[C:20]-[O;H0;D2;+0:18]-[c:21]1:[c:22]:[c:23]:[c:24]:[c;H0;D3;+0:17](-[NH;D2;+0:2]-[c;H0;D3;+0:3]2... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3,4-ethylenedioxyaniline were reacted to yield N2,N4-bis(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.88 (d, 1H, J=3.6 Hz), 7.23 (d, 1H, J=2.3 Hz), 7.15 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Primary amine | Ether.Ether.Ether.Ether.Secondary amine.Secondary amine | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85321b3c9c4e4cf1ad0f9d70db02c906 | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1OC | ClC1=NC=C(C(=N1)Cl)F.COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)OC)F | [CH3:1][O:2][c:18]1[cH:17][cH:3][c:6]([NH2:7])[cH:24][c:21]1[O:22][CH3:23].Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13](Cl)[n:14]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]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]3)[n:25]2)[cH:26][c:27]1[O:28][C... | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Cl | COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1444f1bd808343c5891de9c1d438142751b86c34e0b18418617362e9d1eca832 | 65b82f0cb62f00ee1ea4ef09670b24bbe4757060c21568566ac82512d875d75b | 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].[#8:8]-[c:9]1:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[NH2;D1;+0:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]:1-[O;H0;D2;+0:16]-[C;D1;H3:17]>>[#8:8]-[c:9]1:[cH;D2;+0:10]:[c:18](-[NH;D2;+0:2]-[c;H0;D3;+0:1]2:[#7;a:19]:[c;H0;D3;+0:3](-[NH... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3,4-dimethoxyaniline were reacted to yield N2,N4-bis(3,4-dimethoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.90 (d, 1H, J=1.8 Hz), 7.13 (d, 2H, J=4.8 Hz), 7.08 (d, 1H, J=8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary amine | Ether.Ether.Ether.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1ccc(N)cc1OC.Fc1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a18f3de893b4a23b8132ab65dbf4510 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)cc1>>Fc1cnc(Nc2ccc(Cl)cc2)nc1Nc1ccc(Cl)cc1 | ClC1=NC=C(C(=N1)Cl)F.ClC1=CC=C(N)C=C1>>ClC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)Cl)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:15]([Cl:21])[n:6]1.[cH:7]1[cH:12][c:10]([Cl:11])[cH:19][cH:18][c:17]1[NH2:16]>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[n:14][c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)cc1 | Fc1cnc(Nc2ccc(Cl)cc2)nc1Nc1ccc(Cl)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f47347427b82ac6584f7e75ea6a32d4c439f4cf079868bd64a16e2fab13073c1 | ca42eedb2d2abde17182925596348e291627f72a499b39a7740852f1a7652f06 | 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;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[Cl;D1;H0:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[NH2;D1;+0:14]):[c:15]:[cH;D2;+0:16]:1>>[Cl;D1;H0:9]-[c;H0;D3;+0:10]1:[c:17]:[c:18]:[c;H0;D3;+0:12](-[NH;D2;+0:8]-[c;H0;D3;+0:1]2:[#7;a:19]:[... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-chloroaniline were reacted to yield N2,N4-bis(4-chlorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3+CD3OD): δ 7.80 (d, 1H, J=4.2 Hz), 7.45 (d, 2H, J=8.7 Hz), 7.33 (d, 2H, J=9 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(Cl)cc1>>Fc1cnc(Nc2ccc(Cl)cc2)nc1Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9daeb984c294afe9334e0afeced1816 | Fc1cnc(Cl)nc1Cl.Nc1cccc(Cl)c1>>Fc1cnc(Nc2cccc(Cl)c2)nc1Nc1cccc(Cl)c1 | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=CC1>>ClC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)Cl)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:15]([Cl:22])[n:6]1.[cH:7]1[cH:10][c:11]([Cl:12])[cH:13][c:17]([NH2:16])[cH:18]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]([Cl:12])[cH:13]2)[n:14][c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(Cl)c1 | Fc1cnc(Nc2cccc(Cl)c2)nc1Nc1cccc(Cl)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5e80dec7f0cdd3a4e0877c6ec20345b569333b8c7b92129d20341072eb9b2a9c | e26f3bc6782c001a4124d796c0b9c909acbd5566ad8239681534b58d894ddf93 | 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;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[Cl;D1;H0:9]-[c:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[NH2;D1;+0:15]):[cH;D2;+0:16]:1>>[Cl;D1;H0:9]-[c:10]1:[cH;D2;+0:11]:[c:17]:[c:18]:[c;H0;D3;+0:12](-[NH;D2;+0:8]-[c;H0;D3;+0:1]2:[#7;a:19... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-chloroaniline were reacted to yield N2,N4-bis(3-chlorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.08 (d, 1H, J=5.4 Hz), 7.70 (t, 1H, J=1.8 Hz), 7.57 (t, 1H, J=1.2 Hz), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(Cl)c1>>Fc1cnc(Nc2cccc(Cl)c2)nc1Nc1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd55043166844381a44074a5718fb124 | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc(C(C)(C)C)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)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=CC=C(C=C1)C(C)(C)C)F | [CH3:1][C:2]([c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:28][cH:29]1)([CH3:17])[CH3:21].Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15](Cl)[n:16]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][c:17]3[cH:18][cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]... | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc(C(C)(C)C)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | 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;D1;H3:8]-[C;H0;D4;+0:9](-[CH3;D1;+0:10])(-[CH3;D1;+0:11])-[c:12]1:[c:13]:[c:14]:[c:15](-[NH2;D1;+0:16]):[c:17]:[c:18]:1>>[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:19])(-[C;D1;H3:20])-[c:12]1:[c:13]:[c:14]:[c:15](-[NH;D2;+0:16]-[c;H... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-tert-butylaniline were reacted to yield N2,N4-bis(4-tert-butylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.77 (d, 1H, J=3.9 Hz), 7.47 (d, 2H, J=9 Hz), 7.38 (m, 4H), 7.30 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CC(C)(C)c1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)c1ccc(Nc2ncc(F)c(Nc3ccc(C(C)(C)C)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c7ef0706dd2469c93eb3a0db3bfaba0 | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(Cl)c1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)c(Cl)c3)n2)cc1Cl | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=CC1F>>ClC=1C=C(C=CC1F)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)F)Cl)F | Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([Cl:20])[n:13]1.[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:23][c:24]1[Cl:25]>>[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]([F:18])[c:19]([Cl:20])[cH:21]3)[n:22]2)[cH:23][c:24]1[Cl:25] | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(Cl)c1 | Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)c(Cl)c3)n2)cc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a9ad3594257444e67be3072172dd8ca8dee60a5967b12584a869988d32d8d524 | 71bdaf319506958d57c5c2a4d0fa359b5955b49507e9c65dc64832c95a2dc5ae | 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;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;H0;D1;+0:7]-[c:13](:[c:14]):[c:15]:[c:16](-[NH;D2;+0:8]-[c;H0;D3;+0:6]1:[#7;a:17]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:[c:3]:[c:4]:1-[F;D1;H0:5]):[c:... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-chloro-4-fluoroaniline were reacted to yield N2,N4-bis(3-chloro-4-fluorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3+CD3OD)): δ 7.81 (d, 1H), 7.60 (m, 1H), 7.58 (m, 1H), 7.38 (m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)c(Cl)c1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)c(Cl)c3)n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b8e97d31d164997b8184f48589a6c05 | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)cc1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)F.FC1=CC=C(N)C=C1>>FC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)F)F | Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12](Cl)[n:13]1.[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:22][cH:23]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]([F:18])[cH:19][cH:20]3)[n:21]2)[cH:22][cH:23]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)cc1 | Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f318450f6437a0cd139a0b7cb26f676be1af5a1755b758113450b463628f30cd | e26f3bc6782c001a4124d796c0b9c909acbd5566ad8239681534b58d894ddf93 | 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:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-fluoroaniline were reacted to yield N2,N4-bis(4-fluorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.79 (d, 2H, J=5.4 Hz), 7.40 (m, 2H), 7.30 (m, 2H), 6.90 (m, 4H); 19NMR (C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(F)cc1>>Fc1ccc(Nc2ncc(F)c(Nc3ccc(F)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9b606c4371e459da434a2b6e607eae2 | Cc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)F.CC1=CC=C(N)C=C1>>CC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C)F | [cH:1]1[c:5]([NH2:6])[cH:22][cH:23][c:17]([CH3:18])[cH:19]1.Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12](Cl)[n:21]1>>[CH3:1][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]([CH3:18])[cH:19][cH:20]3)[n:21]2)[cH:22][cH:23]1 | Cc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 17063f9790599d9363915ef3b96d7a5711afaaf38fdeacf6e3cc163a0b39b4e5 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C;D1;H3:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[NH2;D1;+0:13]):[c:14]:[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c:16]:[c:17]:[c:18](-[#7:19]-[c;H0;D3;+0:1]2:[#7;a:2]:[c;H0;D3;+0:3](-[NH;D2;+0:13]-[c;H0;D3;+0... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-methylaniline were reacted to yield N2,N4-bis(4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.73 (d, 1H, J=4.2 Hz), 7.43 (d, 2H, J=8.1 Hz), 7.36 (d, 2H, J=8.4 Hz), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Cc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0abae3015364c6a8c94c765f0aa8a2f | CC(=O)Cl.CC(=O)Oc1cccc(-c2nc(N)nc(N)c2F)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(C)=O)c3)n2)c1 | C(C)(=O)OC=1C=C(C=CC1)C1=C(C(=NC(=N1)N)N)F.OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C)(=O)Cl.N1=CC=CC=C1>>C(C)(=O)OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OC(C)=O)F | Cl[C:24]([CH3:25])=[O:26].Nc1nc(N)c(F)c(-c2cccc(O[C:2]([CH3:1])=[O:3])c2)n1.[OH: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][cH:21][c:22]([OH:23])[cH:27]3)[n:28]2)[cH:29]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][... | CC(=O)Cl.CC(=O)Oc1cccc(-c2nc(N)nc(N)c2F)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | CC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(C)=O)c3)n2)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | e76da7bc4cb26fc9db26070dd8f36010effa73b0335ec067a751fa221a7ebdfd | 97a147dbf1769958cc16ccacf202e0dba1bebdcda4d922d7003ca4b638429b1f | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].F-c1:c(-N):n:c(-N):n:c:1-c1:c:c:c:c(-O-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6]):c:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:5]-[C;H0;D3;+0:4](=[O;D1;H0:6])-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14].[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3]... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-acetoxyaniline were reacted to yield N2,N4-bis[(3-acetoxyphenyl]-5-fluoro-2,4-pyrimidinediamine. Alternatively, N2,N4-bis[(3-acetoxyphenyl]-5-fluoro-2,4-pyrimidinediamine can be prepared... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Ester.Aromatic alcohol.Aromatic alcohol.Primary amine.Primary amine | Ester.Ester | c1cncnc1.c1ccccc1 | null | c1ccccc1.c1cncnc1.c1ccccc1 | HF | C(Cl)Cl | null | null | CC(=O)Cl.CC(=O)Oc1cccc(-c2nc(N)nc(N)c2F)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>C(Cl)Cl>CC(=O)Oc1cccc(Nc2ncc(F)c(Nc3cccc(OC(C)=O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8f2b9cee0204f0da0da7c00ae09e405 | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCc2ccccc2)c1>>Fc1cnc(Nc2cccc(OCc3ccccc3)c2)nc1Nc1cccc(OCc2ccccc2)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C1=CC=CC=C1)OC=1C=C(N)C=CC1>>C(C1=CC=CC=C1)OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OCC1=CC=CC=C1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:22](Cl)[n:21]1.[cH:7]1[cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][cH:9][cH:8][c:24]([NH2:23])[cH:20]2)[cH:19][cH:18][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]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20]2)[n:21][c:22]1[NH:23][c:24]1[... | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCc2ccccc2)c1 | Fc1cnc(Nc2cccc(OCc3ccccc3)c2)nc1Nc1cccc(OCc2ccccc2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1a4e1bd40eb8f6b23c44c9ed6d242eec8e5cef6bfa734ca516774985033b94fd | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | c1ccc(COc2cccc(Nc3ccnc(Nc4cccc(OCc5ccccc5)c4)n3)c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a: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](-[#8:12]-[C:13]-[c:14]2:[c:15]:[c:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:2):[c:20]:[c:21]:[cH;D2;+0:22]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[#7:23]-[c;H0;D3;+0:18... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-benzyloxyaniline were reacted to yield N2,N4-bis(3-benzyloxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.98 (bs, 1H), 7.42-6.99 (m, 16H), 6.75 (d, 1H, J=2.4 Hz), 6.71 (m, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCc2ccccc2)c1>>Fc1cnc(Nc2cccc(OCc3ccccc3)c2)nc1Nc1cccc(OCc2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34777ceca81c4dd7a7fded3d9bc669b3 | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1>>Fc1cnc(Nc2cccc(-c3ccccc3)c2)nc1Nc1cccc(-c2ccccc2)c1 | ClC1=NC=C(C(=N1)Cl)F.C1(=CC=CC=C1)C=1C=C(N)C=CC1>>C1(=CC=CC=C1)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C1=CC=CC=C1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:20](Cl)[n:6]1.[cH:7]1[cH:15][cH:9][cH:8][c:27](-[c:26]2[cH:25][cH:24][cH:23][c:22]([NH2:21])[cH:33]2)[cH:28]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][cH:14][cH:15][cH:16][cH:17]3)[cH:18]2)[n:19][c:20]1[NH:21][c:22]1[cH:23][cH:24][cH:25][c:26](... | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1 | Fc1cnc(Nc2cccc(-c3ccccc3)c2)nc1Nc1cccc(-c2ccccc2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4698d0c089922d648d66c28d6ab78b0260fc086b4ee022ae94a621fb440444cd | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(-c2cccc(Nc3ccnc(Nc4cccc(-c5ccccc5)c4)n3)c2)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:9](:[c:10]):[c:11]:[c:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:1):[c:19]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:2]-[c;H0;D3;+0:15]2:[c:20]:[c... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-phenylaniline were reacted to yield N2,N4-bis[(3-phenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.02 (d, 1H, J=5.1 Hz), 7.82 (t, 1H, J=1.5 Hz), 7.67 (t, 1H, J=1.8 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(-c2ccccc2)c1>>Fc1cnc(Nc2cccc(-c3ccccc3)c2)nc1Nc1cccc(-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc77a0a1184247f6b701db36a1aa1331 | Fc1cnc(Cl)nc1Cl.Nc1ccc2[nH]ccc2c1>>Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2[nH]ccc2c1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C2C=CNC2=CC1>>N1C=CC2=CC(=CC=C12)NC1=NC=C(C(=N1)NC=1C=C2C=CNC2=CC1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:17](Cl)[n:16]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][cH:12][cH:13][c:14]2[cH:15]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[nH:11][cH:12][cH:13][c:14]3[cH:15]2)[n:16][c:17]1[NH:18][c:19]1[cH:20][cH:21][c:22]2[nH:23][cH:24][cH:25][c:26]2[cH:27]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc2[nH]ccc2c1 | Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2[nH]ccc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 820dd806b4849e10051efccfa7e85030015494150c2bcb2e25927813dfc5b98d | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1cc(Nc2ccc3[nH]ccc3c2)nc(Nc2ccc3[nH]ccc3c2)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-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c;H0;D3;+0:1]:1-[#7:12]-[c:13] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 5-aminoindole were reacted to yield N2,N4-bis(indol-5-yl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 20.26 min.; purity: 99%; MS (m/e): 359 (MH+).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2[nH]ccc2c1>>Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97c9420c08d64f58afaa136cabfee59b | CCOC(=O)c1cnc(Cl)nc1Cl.N#CCc1ccc(N)cc1>>CCOC(=O)c1cnc(Nc2ccc(CC#N)cc2)nc1Nc1ccc(CC#N)cc1 | ClC1=NC=C(C(=N1)Cl)C(=O)OCC.C(#N)CC1=CC=C(N)C=C1>>C(#N)CC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)CC#N)C(=O)OCC | Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21](Cl)[n:20]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][C:16]#[N:17])[cH:18][cH:19]1>>[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]([CH2:15][C:16]#[N:17])[cH:18][cH:19]2)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25]... | CCOC(=O)c1cnc(Cl)nc1Cl.N#CCc1ccc(N)cc1 | CCOC(=O)c1cnc(Nc2ccc(CC#N)cc2)nc1Nc1ccc(CC#N)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 48cd90f07e846de4a10ae66fa5d1c64adef201092146c789cc8078ee11044f37 | a2e3dc778b07743897b86c66f8ef0734d28cc7e15b049d580e61cf7ec6fdabc5 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | 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 N2,N4-bis(3-hydroxyphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine, 2,4-dichloro-5-ethoxycarbonylpyrimidine and 4-cyanomethylaniline were reacted to yield N2,N4-bis(4-cyanomethylphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.72 (s, 1H), 7.64 (m, 4H), 7.32 (d, 2H, J=8.7 Hz), 7.21 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Nitrile.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | CCOC(=O)c1cnc(Cl)nc1Cl.N#CCc1ccc(N)cc1>>CCOC(=O)c1cnc(Nc2ccc(CC#N)cc2)nc1Nc1ccc(CC#N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c0f4f6b1fed44f789f8e4065c7e6cce | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2cn[nH]c2c1>>CCOC(=O)c1cnc(Nc2ccc3cn[nH]c3c2)nc1Nc1ccc2cn[nH]c2c1 | ClC1=NC=C(C(=N1)Cl)C(=O)OCC.NC1=CC=C2C=NNC2=C1>>N1N=CC2=CC=C(C=C12)NC1=NC=C(C(=N1)NC1=CC=C2C=NNC2=C1)C(=O)OCC | Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21](Cl)[n:20]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][n:16][nH:17][c:18]2[cH:19]1>>[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[cH:15][n:16][nH:17][c:18]3[cH:19]2)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][c:2... | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2cn[nH]c2c1 | CCOC(=O)c1cnc(Nc2ccc3cn[nH]c3c2)nc1Nc1ccc2cn[nH]c2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9abd1442befdb6dcb90f1aa440b04619413879ea7c4895316f5c1e4583521e6f | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1cc(Nc2ccc3cn[nH]c3c2)nc(Nc2ccc3cn[nH]c3c2)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].[#7;a:11]:[c:12]:[c:13]:[c:14](-[NH2;D1;+0:15]):[c:16]>>[#7;a:11]:[c:12]:[c:13]:[c:14](-[NH;D2;+0:15]-[c;H0;D3;+0:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[#7:17]-[c:18]):[c:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):[c:5]:[#7;a:4]... | null | [] | null | null | null | null | In like manner to N2,N4-bis(3-hydroxyphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine, 2,4-dichloro-5-ethoxycarbonylpyrimidine and 6-aminoindazole were reacted to yield N2,N4-bis(6-indazolyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.76 (s, 1H), 7.73(d, 2H J=8.8), 7.54 (m, 4H), 7.36 (d, 2H, J=9.5 Hz),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccc2n[nH]cc2c1 | c1cncnc1.c1ccc2n[nH]cc2c1.c1ccc2n[nH]cc2c1 | null | null | null | null | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1ccc2cn[nH]c2c1>>CCOC(=O)c1cnc(Nc2ccc3cn[nH]c3c2)nc1Nc1ccc2cn[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa940073e92e457597f64ce9754e6403 | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1cccc2cn[nH]c12>>CCOC(=O)c1cnc(Nc2cccc3cn[nH]c23)nc1Nc1cccc2cn[nH]c12 | ClC1=NC=C(C(=N1)Cl)C(=O)OCC.NC=1C=CC=C2C=NNC12>>N1N=CC2=CC=CC(=C12)NC1=NC=C(C(=N1)NC=1C=CC=C2C=NNC12)C(=O)OCC | Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21](Cl)[n:20]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][nH:18][c:19]12>>[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][cH:14][c:15]3[cH:16][n:17][nH:18][c:19]23)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:... | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1cccc2cn[nH]c12 | CCOC(=O)c1cnc(Nc2cccc3cn[nH]c23)nc1Nc1cccc2cn[nH]c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9abd1442befdb6dcb90f1aa440b04619413879ea7c4895316f5c1e4583521e6f | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1cc(Nc2ccnc(Nc3cccc4cn[nH]c34)n2)c2[nH]ncc2c1 | 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]1:[#7;a:15]:[#7;a:16]:[c:17]:[c:18]:1>>[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]2:[#7;a:15]:[#7;a:16]:[c:17]:[c... | null | [] | null | null | null | null | In like manner to N2,N4-bis(3-hydroxyphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine, 2,4-dichloro-5-ethoxycarbonylpyrimidine and 7-aminoindazole were reacted to yield N2,N4-bis(7-indazolyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.70 (s, 1H), 7.54 (d, 2H J=8.4 Hz), 7.37 (m, 6H), 4.3 (q, 2H, J=7.0 H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccc2n[nH]cc2c1 | c1cncnc1.c1ccc2n[nH]cc2c1.c1ccc2n[nH]cc2c1 | null | null | null | null | CCOC(=O)c1cnc(Cl)nc1Cl.Nc1cccc2cn[nH]c12>>CCOC(=O)c1cnc(Nc2cccc3cn[nH]c23)nc1Nc1cccc2cn[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2bf8efea91646dab1ce3d32e9d4e6fa | Cc1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Cc1cnc(Nc2cccc(O)c2)nc1Nc1cccc(O)c1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)C.OC=1C=C(N)C=CC1>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)C | Cl[c:5]1[n:4][cH:3][c:2]([CH3:1])[c:15](Cl)[n:14]1.[NH2:16][c:17]1[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:23]1.Oc1cccc(Nc2nc([NH:6][c:7]3[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]3)ncc2F)c1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]2)[n:14][c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:... | Cc1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Cc1cnc(Nc2cccc(O)c2)nc1Nc1cccc(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 38b6122167c9a133791a4b41cc24430e7552efb07dd01c4f1a1184dbafa4ede3 | ae8208c81be8121006c7cce142e4356e102a3280f2c27e8b86658cbf7f54594a | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | 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;D1;H3:7].F-c1:c:n:c(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):n:c:1-N-c1:c:c:c:c(-O):c:1.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:1... | null | [] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,4-dichloro-5-methylpyrimidine with 3-hydroxyaniline gave N2,N4-bis(3-hydroxyphenyl)-5-methyl-2,4-pyrimidinediamine. LCMS: ret. time: 16.76 min.; purity: 100%, MS (m/e): 309 (MH+).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HF | null | null | null | Cc1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Cc1cnc(Nc2cccc(O)c2)nc1Nc1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d18369ba1b242b2a937d302b2a7e52a | Clc1ccnc(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ccnc(Nc3cccc(O)c3)n2)c1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=CC(=N1)Cl.OC=1C=C(N)C=CC1>>OC=1C=C(C=CC1)NC1=NC=CC(=N1)NC1=CC(=CC=C1)O | Cl[c:8]1[cH:9][cH:10][n:11][c:12](Cl)[n:21]1.[NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]1.Oc1cccc(Nc2nc([NH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:22]3)ncc2F)c1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]3)[n:21]... | Clc1ccnc(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Oc1cccc(Nc2ccnc(Nc3cccc(O)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 38b6122167c9a133791a4b41cc24430e7552efb07dd01c4f1a1184dbafa4ede3 | ae8208c81be8121006c7cce142e4356e102a3280f2c27e8b86658cbf7f54594a | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-Cl):[#7;a:6]:1.F-c1:c:n:c(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):n:c:1-N-c1:c:c:c:c(-O):c:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:6]:1):[c:14] | null | [] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,4-dichloropyrimidine with 3-hydroxyaniline gave N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine. LCMS: ret. time: 16.21 min.; purity: 100%; MS (m/e): 295 (MH+).
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HF | null | null | null | Clc1ccnc(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ccnc(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2831101e90eb4933a766f844b86f5811 | COc1ccc(N)cc1OC.O=[N+]([O-])c1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OC)c(OC)c3)n2)cc1OC | ClC1=NC=C(C(=N1)Cl)[N+](=O)[O-].COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)OC)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:28][c:29]1[O:30][CH3:31].Cl[c:8]1[n:9][cH:10][c:11]([N+:12]([O-:13])=[O:24])[c:15](Cl)[n:16]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]([N+:12](=[O:13])[O-:14])[c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([O:21][CH3:22])[c:23]([O:24][CH3:25])[cH:26]... | COc1ccc(N)cc1OC.O=[N+]([O-])c1cnc(Cl)nc1Cl | COc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OC)c(OC)c3)n2)cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 59c49963a2133ca6e07a0737762753749a158b36499763886dbdfd05da244aae | fbce72d1ee32b424383145452d048291593afa0b293e44bd4df1444e02e99360 | 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-[N+;H0;D3:7](-[O-;H0;D1:8])=[O;H0;D1;+0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:14]-[O;H0;D2;+0:9]-[c:15](:[c:16]):[c:17]:[c:18](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[#7;a:19]:[c;H0;D3;+0:3](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:4]:... | 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-nitropyrimidine with 3,4-dimethoxyaniline gave N2,N4-bis-(3,4-dimethoxyphenyl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 28.30 min.; purity: 100%; MS (m/e): 428 (MH+); 1H NMR (CDCl3): δ 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitro group.Primary amine | Ether.Ether.Nitro group.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COc1ccc(N)cc1OC.O=[N+]([O-])c1cnc(Cl)nc1Cl>>COc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OC)c(OC)c3)n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17550f6e854b4e2ca09296843bf0c9b0 | CCOc1ccc(N)cc1.O=[N+]([O-])c1cnc(Cl)nc1Cl>>CCOc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OCC)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)[N+](=O)[O-].C(C)OC1=CC=C(N)C=C1>>C(C)OC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:28][cH:29]1.Cl[c:9]1[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16](Cl)[n:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]([O:22][CH2:23][CH3:24])[cH:25][cH:26]3)[n... | CCOc1ccc(N)cc1.O=[N+]([O-])c1cnc(Cl)nc1Cl | CCOc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OCC)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 62f223343fbca7566af616417c883149b0507fc398dcae296734119b0aa5bf8e | e1c501f9a2bc29975aabc09070bf4dffd0e1b08e5b0f3a949d96e7aa889ec0e7 | 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-[#7;+:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;+:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:13](:[c:14]):[c:15] | 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-nitropyrimidine with 4-ethoxyaniline gave N2,N4-bis-(4-ethoxyphenyl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 35.91 min.; purity: 100%; MS (m/e): 396 (MH+); 1H NMR (CDCl3): δ 10.25 (1H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Ether.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CCOc1ccc(N)cc1.O=[N+]([O-])c1cnc(Cl)nc1Cl>>CCOc1ccc(Nc2ncc([N+](=O)[O-])c(Nc3ccc(OCC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69755cf4d2b94ff2a7006f632837af2d | Nc1ccc2c(c1)OCCO2.O=[N+]([O-])c1cnc(Cl)nc1Cl>>O=[N+]([O-])c1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)Cl)[N+](=O)[O-].C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)[N+](=O)[O-] | [NH2:21][c:22]1[cH:23][cH:24][c:25]2[c:26]([cH:27]1)[O:28][CH2:29][CH2:30][O:31]2.Cl[c:7]1[n:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:20](Cl)[n:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[O:15][CH2:16][CH2:17][O:18]3)[n:19][c:20]1[NH:21][c:22]1[cH:23][cH:24][c:25]2[c:... | Nc1ccc2c(c1)OCCO2.O=[N+]([O-])c1cnc(Cl)nc1Cl | O=[N+]([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-[#7;+:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;+:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[#7:12]-[c:13]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 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-nitropyrimidine with 3,4-ethylenedioxyaniline gave N2,N4-bis-(3,4-ethylenedioxyphenyl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 30.78 min.; purity: 100%; MS (m/e): 424 (MH+); 1H NMR (CDC... | 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 | Nc1ccc2c(c1)OCCO2.O=[N+]([O-])c1cnc(Cl)nc1Cl>>O=[N+]([O-])c1cnc(Nc2ccc3c(c2)OCCO3)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f2475f500474d97a2d6c4a7095b175d | Nc1ccc2c(c1)OC(F)(F)O2.O=[N+]([O-])c1cnc(Cl)nc1Cl>>O=[N+]([O-])c1cnc(Nc2ccc3c(c2)OC(F)(F)O3)nc1Nc1ccc2c(c1)OC(F)(F)O2 | ClC1=NC=C(C(=N1)Cl)[N+](=O)[O-].FC1(OC2=C(O1)C=CC(=C2)N)F>>FC1(OC2=C(O1)C=CC(=C2)NC2=NC=C(C(=N2)NC2=CC1=C(OC(O1)(F)F)C=C2)[N+](=O)[O-])F | [C:16]1([F:17])([F:18])[O:29][c:27]2[c:26]([cH:25][cH:24][c:23]([NH2:22])[cH:28]2)[O:33]1.Cl[c:7]1[n:6][cH:5][c:4]([N+:2]([O-:1])=[O:15])[c:9](Cl)[n:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[O:15][C:16]([F:17])([F:18])[O:19]3)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:... | Nc1ccc2c(c1)OC(F)(F)O2.O=[N+]([O-])c1cnc(Cl)nc1Cl | O=[N+]([O-])c1cnc(Nc2ccc3c(c2)OC(F)(F)O3)nc1Nc1ccc2c(c1)OC(F)(F)O2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1dabc896909ad6f9b22bdda2dcf91d1230f95e6b511888e93adad60034093513 | fdd17370903db1e2870e9ac98be4c75784fb37da8a37575489fb436b8d671a92 | c1cc(Nc2ccc3c(c2)OCO3)nc(Nc2ccc3c(c2)OCO3)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-[N+;H0;D3:5](-[O-;H0;D1:6])=[O;H0;D1;+0:7]):[c;H0;D3;+0:8](-Cl):[n;H0;D2;+0:9]:1.[F;D1;H0:10]-[C;H0;D4;+0:11]1(-[F;D1;H0:12])-[O;H0;D2;+0:13]-[c:14]2:[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]:[c:19]:[c:20]:2-[O;H0;D2;+0:21]-1>>[F;D1;H0:10]-[C;H0;D4;+0:11]1(-[F;D1;H0:12])-[#... | 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-nitropyrimidine with 2,2-difluoro-5-amino-1,3-benzodioxole gave N2,N4-bis-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-nitro-2,4-pyrimidinediamine. LCMS: ret. time: 38.15 min.; purity: 96%; MS (m/e): ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary halide.Tertiary halide.Ether.Ether.Nitro group.Primary amine | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ether.Ether.Ether.Ether.Nitro group.Secondary amine.Secondary amine | c1ccc2c(c1)OCO2.c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCO2.c1ccc2c(c1)OCO2 | c1cncnc1.c1ccc2c(c1)OCO2.c1ccc2c(c1)OCO2 | null | null | null | null | Nc1ccc2c(c1)OC(F)(F)O2.O=[N+]([O-])c1cnc(Cl)nc1Cl>>O=[N+]([O-])c1cnc(Nc2ccc3c(c2)OC(F)(F)O3)nc1Nc1ccc2c(c1)OC(F)(F)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d1aff1dfd5e49c786340f2d320de5fc | Fc1cnc(Cl)nc1Cl.Nc1cc(Cl)c(O)c(Cl)c1>>Oc1c(Cl)cc(Nc2ncc(F)c(Nc3cc(Cl)c(O)c(Cl)c3)n2)cc1Cl | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=C(C1O)Cl>>ClC=1C=C(C=C(C1O)Cl)NC1=NC=C(C(=N1)NC1=CC(=C(C(=C1)Cl)O)Cl)F | [c:8]1([Cl:27])[n:9][cH:10][c:11]([F:12])[c:13]([Cl:18])[n:14]1.[OH:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([NH2:7])[cH:23][c:21]1[Cl:22]>>[OH:1][c:2]1[c:3]([Cl: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]([Cl:18])[c:19]([OH:20])[c:21]([Cl:22])[cH:23]3)[n:24]2)[cH:25][c:26]1[Cl:27] | Fc1cnc(Cl)nc1Cl.Nc1cc(Cl)c(O)c(Cl)c1 | Oc1c(Cl)cc(Nc2ncc(F)c(Nc3cc(Cl)c(O)c(Cl)c3)n2)cc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 47572736a6a2b724963372abb54cbe12d6661b54669ea726a21ffe49ca1fbf4b | 165c17b8e1a62e1653e1d20c56d4814470e5234cd167ccfc879c4f405852b486 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[c:6]:[c:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9]:1-[O;D1;H1:10].[Cl;H0;D1;+0:11]-[c;H0;D3;+0:12]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:14](-[Cl;H0;D1;+0:15]):[#7;a:16]:[c:17]:[c:18]:1-[F;D1;H0:19]>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:20](-[NH;D2;+0:13]-[... | 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 with 3,5-dichloro-4-hydroxyaniline gave N2,N4-bis-(3,5-dichloro-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 21.26 min.; purity: 88%; MS (m/e): 450 (M+); 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cc(Cl)c(O)c(Cl)c1>>Oc1c(Cl)cc(Nc2ncc(F)c(Nc3cc(Cl)c(O)c(Cl)c3)n2)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-264a8c3254824303bbddf7ff0db2556e | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)c(Cl)c3)n2)cc(Cl)c1O | ClC1=NC=C(C(=N1)Cl)F.ClC=1C=C(N)C=C(C1O)C>>ClC=1C=C(C=C(C1O)C)NC1=NC=C(C(=N1)NC1=CC(=C(C(=C1)C)O)Cl)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:23][c:24]([Cl:25])[c:26]1[OH:18].Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11]([Cl:20])[n:12]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][c:15]([CH3:16])[c:17]([OH:18])[c:19]([Cl:20])[cH:21]3)[n:22]2)[cH:23][c:24]([Cl:25])[c:26]1[OH:27] | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl | Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)c(Cl)c3)n2)cc(Cl)c1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7ab89a7c37d97576c9698f06e97b1156d9bdceb697c2f8a8a4d4801e5a0ef5fb | 9e9fb60ea5a409de0bb5bf142d224bc507540aaf05abd8f2e2868e287927421b | 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;H0;D1;+0:7]):[n;H0;D2;+0:8]:1.[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]:[c:15](-[Cl;D1;H0:16]):[c;H0;D3;+0:17]:1-[OH;D1;+0:18]>>[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:19]:[c;H0;D3;+0:6](-[NH;D2;+0:8... | 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 with 3-chloro-4-hydroxy-5-methylaniline gave N2,N4-bis-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 20.55 min.; purity: 99%; MS (m/e): 4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine | Aromatic halide.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)c(Cl)c3)n2)cc(Cl)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77876465541c48a7ab2db9bf524b5229 | Cc1c(N)ccc(O)c1C.Fc1cnc(Cl)nc1Cl>>Cc1c(O)ccc(Nc2ncc(F)c(Nc3ccc(O)c(C)c3C)n2)c1C | ClC1=NC=C(C(=N1)Cl)F.CC1=C(N)C=CC(=C1C)O>>CC1=C(C=CC(=C1C)O)NC1=NC=C(C(=N1)NC1=C(C(=C(C=C1)O)C)C)F | [CH3:1][c:2]1[c:23]([CH3:24])[c:16]([OH:4])[cH:3][cH:27][c:26]1[NH2:8].Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14](Cl)[n:15]1>>[CH3:1][c:2]1[c:3]([OH:4])[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]([OH:20])[c:21]([CH3:22])[c:23]3[CH3:24])[n:25]2)[c:26]1[CH3:27] | Cc1c(N)ccc(O)c1C.Fc1cnc(Cl)nc1Cl | Cc1c(O)ccc(Nc2ncc(F)c(Nc3ccc(O)c(C)c3C)n2)c1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8aa71ca130c29252470b6be710f5535092af33c370633482ca0e25038ee8ed70 | 919ef93eebf20026fe7af42235ad03326f3257ecc30454dfe426ac062a966d20 | 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].[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:10](-[C;D1;H3:11]):[c;H0;D3;+0:12](-[OH;D1;+0:13]):[cH;D2;+0:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16]:1-[NH2;D1;+0:17]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c;H0;D3;+0:16](-[CH3;D1;+0:15]):[c:18](-[NH;D2;+0... | 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 with 2,3-dimethyl-4-hydroxyaniline gave N2,N4-bis-(2,3-dimethyl-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 19.07 min.; purity: 99%; MS (m/e): 369 (MH+); ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine | Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Cc1c(N)ccc(O)c1C.Fc1cnc(Cl)nc1Cl>>Cc1c(O)ccc(Nc2ncc(F)c(Nc3ccc(O)c(C)c3C)n2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26321f5bd2ff4c369e89238b34c3017c | CC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(C)=O)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)F.C(C)(=O)NC1=CC=C(N)C=C1>>C(C)(=O)NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)NC(C)=O)F | [CH3:1][C:2](=[O:3])[NH: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](Cl)[n:27]1>>[CH3:1][C:2](=[O:3])[NH: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][c:17]3[cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[cH:25][cH:26]3)[n:27]2)[cH:... | CC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | CC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(C)=O)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2737a7820ee679aa9f90bd686776e5f84ff0c1a08c4a388b5e3c8680ab9b14e1 | fba702614f8c3cc5583a1a229853d63524a61931d5ebc1700c89bd673095bcbf | 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.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:7]:[c;H0;D3;+0:6]:1-[#7:12]-[c:13] | 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 with 4-acetamidoaniline gave N2,N4-bis-(4-acetamidophenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 14.82 min.; purity: 95%; MS (m/e): 395 (MH+); 1H NMR (DMSO-d6): δ 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amide.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(C)=O)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4d9b9f9929f4b93ae07a1968baae488 | CC(C)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CC(C)c1cccc(Nc2ncc(F)c(Nc3cccc(C(C)C)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C)(C)C=1C=C(N)C=CC1>>C(C)(C)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C(C)C)F | [CH3:1][CH:2]([c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:27]1)[CH3:22].Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15](Cl)[n:16]1>>[CH3:1][CH:2]([CH3:3])[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][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25]3)[n:26]2)[cH:27]1 | CC(C)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl | CC(C)c1cccc(Nc2ncc(F)c(Nc3cccc(C(C)C)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | 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;D1;H3:8]-[CH;D3;+0:9](-[CH3;D1;+0:10])-[c:11](:[c:12]):[c:13]:[c:14](-[NH2;D1;+0:15]):[c:16]>>[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:17])-[c:11](:[c:12]):[c:13]:[c:14](-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-isopropylaniline were reacted to give N2,N4-bis-(3-isopropylphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 29.58 min.; Purity: 98%; MS (m/e): 365 (MH+); 1H NMR (DMSO-d6): δ 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CC(C)c1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CC(C)c1cccc(Nc2ncc(F)c(Nc3cccc(C(C)C)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39960555b72b4505b9b842afabf999db | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1>>Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2cc[nH]c2c1 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2C=CNC2=C1>>N1C=CC2=CC=C(C=C12)NC1=NC=C(C(=N1)NC1=CC=C2C=CNC2=C1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:9](Cl)[n:13]1.[NH2:6][c:7]1[cH:8][cH:21][c:22]2[cH:23][cH:24][nH:25][c:26]2[cH:27]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][nH:13][c:14]3[cH:15]2)[n:16][c:17]1[NH:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][cH:24][nH:25][c:26]2[cH:27]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1 | Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2cc[nH]c2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e660b5a8ff79e56549fbf72198974d363edeb477df66acedea285541103a881e | 45ae7d7d2972e3a9d0ff628eb6c7e0cac8c3e39c85da29f5c6439797c3fe97a5 | c1cc(Nc2ccc3cc[nH]c3c2)nc(Nc2ccc3cc[nH]c3c2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-Cl):[n;H0;D2;+0:7]:1.[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]2:[#7;a:12]:[c:13]:[c:14]:[c:15]:2:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[F;D1;H0:5]-[c;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c;H0;D3;+0:9]2:[c:18]:[c:19]3:[... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 6-aminoindole were reacted to yield N2,N4-bis(indol-6-yl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 22.39 min.; purity: 85%; MS (m/e): 359 (MH+).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Secondary amine.Secondary amine | c1cncnc1.c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2cc[nH]c2c1>>Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2cc[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e712860a8834fb48dda438c987dc157 | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5[nH]c(C(=O)OCC)cc5c4)n3)ccc2[nH]1 | ClC1=NC=C(C(=N1)Cl)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)NC=1C=C2C=C(NC2=CC1)C(=O)OCC)F | [CH3:1][CH2:2][O:3][C:25](=[O:5])[c:24]1[nH:23][c:36]2[c:8]([cH:9][c:10]([NH2:11])[cH:34][cH:35]2)[cH:30]1.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17](Cl)[n:18]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:17]([NH:18][c:19]4[cH:20][cH:21][c:22]5[nH:23][c:24... | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Cl | CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5[nH]c(C(=O)OCC)cc5c4)n3)ccc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b5e160e7bf6656b30f7e850414bb2aac5687ecb2bb68a09b6c1cea78287b0dbb | 6552361de42d161b0a08a553c1d23825d7c8b38b72c3b0e48e062893d39afff9 | c1cc(Nc2ccc3[nH]ccc3c2)nc(Nc2ccc3[nH]ccc3c2)n1 | 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;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13]1:[cH;D2;+0:14]:[c;H0;D3;+0:15]2:[c:16]:[c:17](-[NH2;D1;+0:18]):[c:19]:[c:20]:[c;H0;D3;+0:21]:2:[nH;D2;+0:22]:1>>[C:23]-[#8:24]-[C;H0;D3;+0:11](=[O;D1;H0:2... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 2-ethoxycarbonyl-5-indoleamine were reacted to yield N2,N4-bis(2-ethoxycarbonylindol-5-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 11.83 (s, 1H), 11.63 (s, 1H), 9.21 (s, 1H), 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Primary amine | Ester.Ester.Secondary amine.Secondary amine | c1ccc2[nH]ccc2c1.c1cncnc1 | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccc2[nH]ccc2c1 | null | null | null | null | CCOC(=O)c1cc2cc(N)ccc2[nH]1.Fc1cnc(Cl)nc1Cl>>CCOC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5[nH]c(C(=O)OCC)cc5c4)n3)ccc2[nH]1 |
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