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-be7a8b77a5ec47dba358ca1ef030f911 | Fc1cnc(Cl)nc1Cl.Nc1ccc2oc(=O)ccc2c1>>O=c1ccc2cc(Nc3ncc(F)c(Nc4ccc5oc(=O)ccc5c4)n3)ccc2o1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C2C=CC(OC2=CC1)=O>>O1C(=O)C=CC2=CC(=CC=C12)NC1=NC=C(C(=N1)NC=1C=C2C=CC(OC2=CC1)=O)F | Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14](Cl)[n:15]1.[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[cH:28][cH:29][c:16]2[o:20]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]4[cH:17][cH:18][c:19]5[o:20][c:21](=[O:22])[cH:23][cH:24][c:25]5[cH:26]4)[n:27]3)[cH:2... | Fc1cnc(Cl)nc1Cl.Nc1ccc2oc(=O)ccc2c1 | O=c1ccc2cc(Nc3ncc(F)c(Nc4ccc5oc(=O)ccc5c4)n3)ccc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 77c8dcb5e5ee6928214ca1781fefdc1126a3570cc21b8190103f450ebbde22f8 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | O=c1ccc2cc(Nc3ccnc(Nc4ccc5oc(=O)ccc5c4)n3)ccc2o1 | 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]:[cH;D2;+0:11]:[c;H0;D3;+0:12]2:[o;H0;D2;+0:13]:[c;H0;D3;+0:14](=[O;D1;H0:15]):[c:16]:[c:17]:[c;H0;D3;+0:18]:2:[c:19]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c:9]2:[c:10]:[cH;D2... | 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-aminocoumarin were reacted to yield N2,N4-bis(coumarin-6-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.17 (d, 2H, J=3.6 Hz), 7.97-7.74 (m, 5H), 7.40 (1H, d, J=8.7 Hz), 7.30 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccc2occcc2c1 | c1ccc2occcc2c1.c1cncnc1.c1ccc2occcc2c1 | c1ccc2occcc2c1.c1cncnc1.c1ccc2occcc2c1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc2oc(=O)ccc2c1>>O=c1ccc2cc(Nc3ncc(F)c(Nc4ccc5oc(=O)ccc5c4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-649b890008014ae39e858d98547edf10 | COCc1cc(=O)oc2cc(N)ccc12.Fc1cnc(Cl)nc1Cl>>O=c1ccc2ccc(Nc3ncc(F)c(Nc4ccc5ccc(=O)oc5c4)n3)cc2o1 | ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C2C(=CC(OC2=C1)=O)COC>>O1C(=O)C=CC2=CC=C(C=C12)NC1=NC=C(C(=N1)NC1=CC=C2C=CC(OC2=C1)=O)F | [O:1]=[c:2]1[cH:3][c:4]([CH2:19][O:24][CH3:17])[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:29][c:30]2[o:31]1.Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15](Cl)[n:16]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[cH:21][cH:22][c:23](=[O:24])[o:25... | COCc1cc(=O)oc2cc(N)ccc12.Fc1cnc(Cl)nc1Cl | O=c1ccc2ccc(Nc3ncc(F)c(Nc4ccc5ccc(=O)oc5c4)n3)cc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 022380a31872439e3a0adb3f5a3dd7a54d2f19e00f24f7c624692ad9826065f3 | 048b0afcd3fd57de9ba15ad7b795e0762cd3fe4357c9008fb4d84e00a8a2b673 | O=c1ccc2ccc(Nc3ccnc(Nc4ccc5ccc(=O)oc5c4)n3)cc2o1 | 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.[CH3;D1;+0:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[c;H0;D3;+0:11]1:[c:12]:[c:13](=[O;D1;H0:14]):[#8;a:15]:[c:16]2:[c:17]:[c:18](-[NH2;D1;+0:19]):[c:20]:[c:21]:[c:22]:2:1>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:19]-... | 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 7-amino-4-methoxymethylcoumarin were reacted to yield N2,N4-bis(coumarin-7-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.38 (s, 1H), 8.42 (d, 1H, J=3 Hz), 8.28 (m, 1H), 8.05-7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary amine | Secondary amine.Secondary amine | c1ccc2cccoc2c1.c1cncnc1 | c1ccc2cccoc2c1.c1cncnc1.c1ccc2cccoc2c1 | c1ccc2cccoc2c1.c1cncnc1.c1ccc2cccoc2c1 | null | null | null | null | COCc1cc(=O)oc2cc(N)ccc12.Fc1cnc(Cl)nc1Cl>>O=c1ccc2ccc(Nc3ncc(F)c(Nc4ccc5ccc(=O)oc5c4)n3)cc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bae3ca18a944499bda846aeb63461d5 | NCc1ccco1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(NCc2ccco2)nc1NCc1ccco1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)F.C(C1=CC=CO1)N>>C(C1=CC=CO1)NC1=NC=C(C(=N1)NCC1=CC=CO1)F | [NH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][o:21]1.Oc1cccc(N[c:14]2[c:2]([F:1])[cH:3][n:4][c:5]([NH:6][c:7]3c[c:11]([OH:12])[cH:10][cH:9][cH:8]3)[n:13]2)c1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:13][c:14]1[NH:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][o:21]1 | NCc1ccco1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Fc1cnc(NCc2ccco2)nc1NCc1ccco1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 69e6a1f3db001153526c2ae012d227a64237055405f2768df214f7e8f5a84901 | 41ca4a509e15375b8b434c3a54cb9565f1f7020c8c8b50250a9f8167101e66d1 | c1coc(CNc2ccnc(NCc3ccco3)n2)c1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[#7:4]-[c;H0;D3;+0:5]3:[cH;D2;+0:6]:[c:7]:[c:8]:[c;H0;D3;+0:9](-[OH;D1;+0:10]):c:3):[#7;a:11]:[c:12]:[c:13]:2-[F;D1;H0:14]):c:1.[#8;a:15]:[c:16]-[C:17]-[NH2;D1;+0:18]>>[#8;a:15]:[c:16]-[C:17]-[NH;D2;+0:18]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:6... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and furfurylamine were reacted to yield N2,N4-bis(furfuryl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.72 (bs, 1H), 7.38 (dd, 2H, J=1.8 and 7.5 Hz), 6.34-6.30 (m, 2H), 6.22 (dd, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1.c1ccoc1 | HO- | null | null | null | NCc1ccco1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(NCc2ccco2)nc1NCc1ccco1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66ea6aff6a7b41478545a9043fd92ad2 | NCc1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(NCc2ccccc2)nc1NCc1ccccc1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)F.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC1=NC=C(C(=N1)NCC1=CC=CC=C1)F | [NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Oc1cccc(N[c:15]2[c:2]([F:1])[cH:3][n:4][c:5]([NH:6][c:7]3[cH:8][cH:13][cH:12][c:11](O)[cH:10]3)[n:14]2)[cH:9]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]1[NH:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c... | NCc1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Fc1cnc(NCc2ccccc2)nc1NCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 73cc58a1d64a9d739e4fea908cbcdf4e1308c6079b4124d7c0df58edb1ade386 | 41ca4a509e15375b8b434c3a54cb9565f1f7020c8c8b50250a9f8167101e66d1 | c1ccc(CNc2ccnc(NCc3ccccc3)n2)cc1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[#7:6]-[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-N-c3:[cH;D2;+0:10]:c(-O):c:c:c:3):[c:11](-[F;D1;H0:12]):[c:13]:[#7;a:14]:2):[cH;D2;+0:15]:1.[NH2;D1;+0:16]-[C:17]-[c:18]>>[F;D1;H0:12]-[c:11]1:[c:13]:[#7;a:14]:[c:7](-[#7:6]-[CH2;D2;+0:5]-[c;H0;D3;+0:4]2:[c:3]:[c:2]:[cH;D2... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and benzylamine were reacted to yield N2,N4-bis(benzyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.69 (bs, 1H), 7.35-7.24 (m, 10H), 5.63 (bs, 1H), 5.27 (bs, 1H), 4.61 (d, 2H, J=6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | NCc1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(NCc2ccccc2)nc1NCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c34293099efc4fe0a34d1d9e1c281c21 | Fc1cnc(Cl)nc1Cl.N#Cc1ccc(N)cc1>>N#Cc1ccc(Nc2ncc(F)c(Nc3ccc(C#N)cc3)n2)cc1 | NC1=CC=C(C#N)C=C1.ClC1=NC=C(C(=N1)Cl)F>>C(#N)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C#N)F | Cl[c:8]1[n:1][c:13](Cl)[c:11]([F:12])[cH:10][n:9]1.[cH:2]1[cH:5][c:6]([NH2:7])[cH:24][cH:25][c:18]1[C:19]#[N:20]>>[N:1]#[C: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]([C:19]#[N:20])[cH:21][cH:22]3)[n:23]2)[cH:24][cH:25]1 | Fc1cnc(Cl)nc1Cl.N#Cc1ccc(N)cc1 | N#Cc1ccc(Nc2ncc(F)c(Nc3ccc(C#N)cc3)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f027fb6b282e1f9556c87ad52a62cce8e7a66adf9ca92c0a49fd0af93709172b | a2e3dc778b07743897b86c66f8ef0734d28cc7e15b049d580e61cf7ec6fdabc5 | 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].[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:14]-[c:13]2:[c:12]:[cH;D2;+0:11]:[c:17](-[C;H0;D2;+0:16]#[N;... | null | [] | null | null | null | null | In like manner to the preparation of N2,N-4-bis(3-hydroxyphenyl)-5-fluoro-4-pyrimidineamine, 4-aminobenzonitrile and 2,4-dichloro-5-fluoropyrimidine gave N2,N4-bis(4-cyanophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 7.26 (d, J=8.7 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H), 7.43 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.7 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Nitrile.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.N#Cc1ccc(N)cc1>>N#Cc1ccc(Nc2ncc(F)c(Nc3ccc(C#N)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b57db23d5f9f4abcbfe6be7e53a813ed | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCc1ccc(Nc2ncc(F)c(Nc3ccc(CC)cc3)n2)cc1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)F.C(C)C1=CC=C(N)C=C1>>C(C)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)CC)F | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:24][cH:25]1.O[c:20]1cccc(N[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:21](O)[cH:22]3)[n:23]2)[cH:19]1>>[CH3:1][CH2:2][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]([CH2:19][CH3:20]... | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | CCc1ccc(Nc2ncc(F)c(Nc3ccc(CC)cc3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 73cc58a1d64a9d739e4fea908cbcdf4e1308c6079b4124d7c0df58edb1ade386 | 41ca4a509e15375b8b434c3a54cb9565f1f7020c8c8b50250a9f8167101e66d1 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | O-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:c(-N-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]):c:c:c:1.O-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:[cH;D2;+0:8]:1.[c:7]:[#7;a:6]:[c;H0;D3;+0:3](-[NH;D2;+0:... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-ethylaniline were reacted to yield N2,N4-bis(4-ethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.83 (bs, 1H), 7.77 (d, 1H. J=3.9 Hz), 7.48 (d, 2H, J=8.7 Hz), 7.40 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCc1ccc(Nc2ncc(F)c(Nc3ccc(CC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-392e621c7ee4416b98ab1ec9ce794d2a | Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Nc1ncc(F)c(N)n1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)F.C(C)(C)OC1=CC=C(N)C=C1>>FC=1C(=NC(=NC1)N)N | Oc1cccc([NH:1][c:2]2[n:3][cH:4][c:5]([F:6])[c:7]([NH:8]c3cccc(O)c3)[n:9]2)c1>>[NH2:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([NH2:8])[n:9]1 | Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Nc1ncc(F)c(N)n1 | null | null | null | Reduction | OtherReaction | 0016ef7a90e372decb45296a1b7cde8e8488caf9a73d23a4aca3c6058b9a3202 | 9224a450bb292a3abc4deab50f9512836f816807ad66edd148beae7375e65493 | c1cncnc1 | O-c1:c:c:c:c(-[NH;D2;+0:1]-[c:2]2:[#7;a:3]:[c:4]:[c:5]:[c:6](-[NH;D2;+0:7]-c3:c:c:c:c(-O):c:3):[#7;a:8]:2):c:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[#7;a:8]:1 | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-isopropoxyaniline were reacted to yield N2,N4-bis(4-isopropoxy)phenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.89 (bs, 1H), 7.47 (d, 2H, J=8.7 Hz), 7.38 (d, 2H, J=9.0 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | Primary amine.Primary amine | c1ccccc1.c1ccccc1 | null | c1cncnc1 | HO- | null | null | null | Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Nc1ncc(F)c(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94780eb23ba54e9cbc8b7418c23e2f53 | Clc1ncc(Br)c(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.BrC=1C(=NC(=NC1)Cl)Cl.NC=1C=C(C=CC1)O>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)Br | Cl[c:8]1[n:9][cH:10][c:11]([Br:12])[c:13](Cl)[n:22]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:23]1.Oc1cccc(Nc2nc([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21]3)ncc2F)c1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([Br:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([OH:20]... | Clc1ncc(Br)c(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Oc1cccc(Nc2ncc(Br)c(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;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[Br;D1;H0:7].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]>>[Br;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 5-bromo-2,4-dichloropyrimidine and 3-aminophenol were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.99 (bs, 1H), 9.34 (bs, 1H), 8.30 (s, 1H), 7.15 (t, 1H, J=8.4 Hz), 7.... | 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 | Clc1ncc(Br)c(Cl)n1.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(Br)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d98607b8d8844d069d212e2fe25cb5cf | N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>N#Cc1c(N)nc(N)nc1-c1cccc(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#N.OC=1C=C(N)C=CC1>>OC=1C=C(C=CC1)C1=C(C(=NC(=N1)N)N)C#N | Cl[c:4]1[c:3]([C:2]#[N:1])[cH:10][n:9][c:7](Cl)[n:6]1.Oc1cccc(Nc2nc(N[c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]3)[n:5]cc2F)c1>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([NH2:8])[n:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1 | N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | N#Cc1c(N)nc(N)nc1-c1cccc(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 604d30cd30dea219cfbb29f39bc01565c740242636e74329e3212a1f4b94fd30 | deaec186888f12dfad49cdfe0abe451b87032bc902636b0984f2393923bd86c8 | c1ccc(-c2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[cH;D2;+0:5]:[c:6]:1-[C:7]#[N;D1;H0:8].F-c1:c:[n;H0;D2;+0:9]:c(-N-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):n:c:1-N-c1:c:c:c:c(-O):c:1>>[N;D1;H0:8]#[C:7]-[c:6]1:[c;H0;D3;+0:5](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[#7;a:4]:[c;H0;D3;+0:3](-[N;D1;H2:... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-cyanopyrimidine and 3-hydroxyaniline were reacted to yield N2,N4-bis(3-hydroxyphenyl-5-cyano-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.73 (bs, 1H), 9.40 (s, 1H), 9.33 (bs, 1H), 9.24 (s, 1H), 8.47 (s, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Secondary amine.Secondary amine | Primary amine.Primary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HF | null | null | null | N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>N#Cc1c(N)nc(N)nc1-c1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5463f0ac24ac4ceda20ec0ddef8dca4d | CCOC(=O)Cc1ccc(N)cc1.N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCOC(=O)Cc1ccc(Nc2ncc(C#N)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)C#N.NC1=CC=C(C=C1)CC(=O)OCC>>C(C)OC(=O)CC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)CC(=O)OCC)C#N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:33][cH:34]1.Cl[c:12]1[n:13][cH:14][c:15]([C:16]#[N:17])[c:18](Cl)[n:32]1.Fc1cnc([NH:19][c:23]2[cH:22][cH:21][cH:20][c:25]([OH:26])[cH:24]2)nc1N[c:30]1cc[cH:29][c:28]([OH:27])[cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c... | CCOC(=O)Cc1ccc(N)cc1.N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | CCOC(=O)Cc1ccc(Nc2ncc(C#N)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 | null | null | null | Acylation | OtherReaction | 549d2ff1e11d0be5fb33800399fd9792b796eb2d13cf58583e2c068a7dc76d57 | 848aa6ac84a9071da4cd0ad789597c97be76472b2af033c4d066bfa4910ca45d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]#[N;D1;H0:6]):[c;H0;D3;+0:7](-Cl):[#7;a:8]:1.F-c1:c:n:c(-[NH;D2;+0:9]-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[OH;D1;+0:15]):[cH;D2;+0:16]:2):n:c:1-N-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[c;H0;D3;+0:19](-[OH;D1;+0:20]):[cH;D2;+0:21]:c:c:1.[NH2;D1;+0:22]-[c:2... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-cyanopyrimidine and ethyl 4-aminophenylacetate were reacted to yield N2,N4-bis[4-(ethoxycarbonylmethyl)phenyl]-5-cyano-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.29 (bs, 1H), 7.46 (2d, 4H, J=7.8 Hz), 7.28... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine | Ester.Secondary amine.Secondary amine | c1cncnc1.c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HF | null | null | null | CCOC(=O)Cc1ccc(N)cc1.N#Cc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCOC(=O)Cc1ccc(Nc2ncc(C#N)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd56e204bd74431eb65cb8c4ca87fee4 | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCCO)c1>>OCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCO)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(OCCO)C=CC1>>OCCOC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OCCO)F | Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16](Cl)[n:17]1.[O:1]([CH2:2][CH2:25][OH:26])[c:22]1[cH:21][cH:20][cH:19][c:9]([NH2:10])[cH:27]1>>[OH:1][CH2:2][CH2:3][O: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]([O:23][CH2:24][CH2:25][OH:26])[cH:27]3)... | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCCO)c1 | OCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCO)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 030825df94ddc443ad8e06aacf3bab9d1cb39918b31684ae7683086c0a5e3519 | c0b6692bb3199267bed23cec30f2dd67922ef6ef5854a0a466fe1453917a2103 | 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;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[c;H0;D3;+0:13](-[O;H0;D2;+0:14]-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[O;D1;H1:17]):[cH;D2;+0:18]:1>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c;H0;D3;+0:9]... | 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-(3-aminophenoxy)ethanol were reacted to produce N2,N4-bis[3-(2-hydroxyethoxy)phenyl]-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.50 (br s, 1H), 9.35 (br s, 1H), 8.13 (d, 1H, J=... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary alcohol.Primary amine | Ether.Ether.Primary alcohol.Primary alcohol.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(OCCO)c1>>OCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCO)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17c75a4d38e245b9b9c07a9260b98a13 | COCCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>COCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCOC)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.COCCOC=1C=C(N)C=CC1>>COCCOC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)OCCOC)F | [CH2:1]([O:2][c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:31]1)[CH2:26][O:27][CH3:28].Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17](Cl)[n:30]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]3[cH:20][cH:21][cH:22][c:23]([O:24][CH2:25][CH2:26][O:27]... | COCCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl | COCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCOC)c3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | eb81ee4c7466e9fa77116cfea89934b0dce362e13882cbbfce573cb4948eadaa | 803f8514cb09365110cfadee6d865ca3b804582a022196c598b58ac3ea09b716 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[C;D1;H3:8]-[#8:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:13]1:[c:14]:[c:15](-[NH2;D1;+0:16]):[c:17]:[c:18]:[c:19]:1>>[#8:20]-[C:21]-[CH2;D2;+0:10]-[#8:9]-[C;D1;H3:8].[CH3;D1;+0:11]-[O;H0;D2;+0:12]-[C:22]-[C:23]-[#8:... | 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-(2-methoxyethoxy)aniline were reacted to produce N2,N4-bis[3-(2-methoxyethyl)oxyphenyl]-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.96 (d, 1H, J=2.9 Hz), 7.36 (t, 1H, J=1.7 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Primary amine | Ether.Ether.Ether.Ether.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | COCCOc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>COCCOc1cccc(Nc2ncc(F)c(Nc3cccc(OCCOC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6fc4fd0b5e742e49e22584ff3b5887a | CC(C)c1ccc(O)cc1N.Fc1cnc(Cl)nc1Cl>>CC(C)c1ccc(O)cc1Nc1ncc(F)c(Nc2cc(O)ccc2C(C)C)n1 | NC=1C=C(C=CC1C(C)C)O.ClC1=NC=C(C(=N1)Cl)F>>OC=1C=CC(=C(C1)NC1=NC=C(C(=N1)NC1=C(C=CC(=C1)O)C(C)C)F)C(C)C | [CH3:1][CH:2]([c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][c:10]1[NH2:18])[CH3:21].Cl[c:12]1[n:11][c:17](Cl)[c:15]([F:16])[cH:14][n:13]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][c:21]([OH:22])[cH:23][cH:24][c:25]2[CH:26]([CH3:27])[... | CC(C)c1ccc(O)cc1N.Fc1cnc(Cl)nc1Cl | CC(C)c1ccc(O)cc1Nc1ncc(F)c(Nc2cc(O)ccc2C(C)C)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4f8bec20a26192387ad3e1a0fad6c4cc8e1c2927688d7dffc25e0e97e26763f6 | 21ac61801f680a0fd4713aa79572457ec8c95552d1bd22e84dee389ea1fa0604 | 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;H0;D3;+0:13](-[NH2;D1;+0:14]):[c:15]:[c:16]>>[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:17])-[c:11](:[c:12]):[c;H0;D3;+0:13](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 3-amino-4-isopropylphenol and 2,4-dichloro-5-fluoropyrimidine were reacted to produce N2,N4-bis(5-hydroxy-2-isopropylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.93 (d, 1H, J=3.5 Hz), 7.79 (br s, 1H), 7.64 (br... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic alcohol.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | null | null | null | CC(C)c1ccc(O)cc1N.Fc1cnc(Cl)nc1Cl>>CC(C)c1ccc(O)cc1Nc1ncc(F)c(Nc2cc(O)ccc2C(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e735127d8a2048989aa348df6a591467 | COC(=O)C=C1C=CC=C(N)C1.Fc1cnc(Cl)nc1Cl>>COC(=O)C=C1C=CC=C(Nc2ncc(F)c(NC3=CC=CC(=CC(=O)OC)C3)n2)C1 | ClC1=NC=C(C(=N1)Cl)F.COC(=O)C=C1CC(N)=CC=C1>>COC(=O)C=C1CC(=CC=C1)NC1=NC=C(C(=N1)NC=1CC(C=CC1)=CC(=O)OC)F | [CH:1]1=[C:12]([NH2:11])[CH2:29][C:23](=[CH:24][C:25](=[O:2])[O:27][CH3:28])[CH:22]=[CH:21]1.Cl[c:17]1[c:15]([F:16])[cH:14][n:13][c:19](Cl)[n:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][c:12]2[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C:19]3=[CH:20][CH:21]=[CH:22][C:23](=[CH:24][C:25](... | COC(=O)C=C1C=CC=C(N)C1.Fc1cnc(Cl)nc1Cl | COC(=O)C=C1C=CC=C(Nc2ncc(F)c(NC3=CC=CC(=CC(=O)OC)C3)n2)C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 32973ed42d410f1ac2211cb02cc987f5292bb8eca9ea3516a00823f9e792c27e | 4ab5024168d103f3355d858ec2aaa1a242d6fb2259ececa3dda51b4dcad17332 | [CH]=C1C=CC=C(Nc2ccnc(NC3=CC=CC(=[CH])C3)n2)C1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C;D1;H3:8]-[#8:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]=[C:13]1-[C:14]=[CH;D2;+0:15]-[CH;D2;+0:16]=[C;H0;D3;+0:17](-[NH2;D1;+0:18])-[CH2;D2;+0:19]-1>>[C:20]-[C:21](-[NH;D2;+0:18]-[c;H0;D3;+0:17]1:[#7;a:22]:[c;H0;D3;+0:1](... | 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-(methoxycarbonylmethylene)aniline were reacted to produce the desired N2,N4-bis(3-methoxycarbonylmethylenephenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.23 (br s, 1H), 10... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Aromatic halide.Ester.Conjugated diene | Enamine.Enamine.Ester.Ester.Conjugated diene.Conjugated diene | C1=CCCC=C1.c1cncnc1 | C1=CCCC=C1.c1cncnc1.C1=CCCC=C1 | C1=CCCC=C1.c1cncnc1.C1=CCCC=C1 | null | null | null | null | COC(=O)C=C1C=CC=C(N)C1.Fc1cnc(Cl)nc1Cl>>COC(=O)C=C1C=CC=C(Nc2ncc(F)c(NC3=CC=CC(=CC(=O)OC)C3)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92fc6d943d374c6a9d36abb743cd6459 | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-].Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC(=C(C(=N1)Cl)[N+](=O)[O-])C(=O)OCC.Cl.C(C)OC(CN)=O>>C(C)OC(=O)CNC1=NC(=C(C(=N1)NCC(=O)OCC)[N+](=O)[O-])C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7].Cl[c:8]1[n:9][c:10](Cl)[c:18]([N+:19](=[O:20])[O-:21])[c:22]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[n:28]1.Fc1cnc([NH:11]c2ccc[c:13]([OH:14])[cH:12]2)nc1Nc1cc[cH:17][c:16]([OH:15])c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[n:9][c:10]([NH:11][CH2:12][C:13](=[O:... | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-].Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1 | null | null | C(C)N(CC)CC | Acylation | OtherReaction | 9a9b2a7419963612e9015fe6d06528945e61791054c1344150d62f1425ef40c0 | 848aa6ac84a9071da4cd0ad789597c97be76472b2af033c4d066bfa4910ca45d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:1-[#7;+:10].F-c1:c:n:c(-[NH;D2;+0:11]-c2:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[OH;D1;+0:14]):c:c:c:2):n:c:1-N-c1:c:c:[cH;D2;+0:15]:[c;H0;D3;+0:16](-[OH;D1;+0:17]):c:1.[C:18]-[#8:19]-[C:20](=[O;D1;H0:21])-[C:22]-[NH2;D1;+0:23]>>[... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, with the addition of triethylamine, 2,4-dichloro-6-ethoxycarbonyl-5-nitropyrimidine and glycine ethyl ester hydrochloride were reacted to yield N2,N4-bis(ethoxycarbonylmethyl)-6-ethoxycarbonyl-5-nitro-2,4-pyrimidinediam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine | Ester.Secondary amine.Secondary amine | c1cncnc1.c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1 | c1cncnc1 | HF | C(C)N(CC)CC | null | null | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-].Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>C(C)N(CC)CC>CCOC(=O)CNc1nc(NCC(=O)OCC)c([N+](=O)[O-])c(C(=O)OCC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-540b17ea67e246ebb6f44d10c14ae653 | FC(F)(F)c1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(C(F)(F)F)c(Nc3cccc(O)c3)n2)c1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)C(F)(F)F.NC=1C=C(C=CC1)O>>OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)C(F)(F)F | Cl[c:8]1[n:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16](Cl)[n:25]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1.Oc1cccc(Nc2ncc(F)c([NH:17][c:18]3[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]3)n2)c1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]([NH:1... | FC(F)(F)c1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Oc1cccc(Nc2ncc(C(F)(F)F)c(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;H0;D3;+0:3](-Cl):[#7;a:4]:[c:5]:[c:6]:1-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10].F-c1:c:n:c(-N-c2:c:c:c:c(-O):c:2):n:c:1-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[F;D1;H0:8]-[C:7](-[F;D1;H0:9])(-[F;D1;H0:10])-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-trifluoromethylpyrimidine and 3-aminophenol were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-trifluoromethyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.82 (bs, 1H), 8.88 (bs, 1H), 8.36 (s, 1H), 7.18-7... | 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 | FC(F)(F)c1cnc(Cl)nc1Cl.Nc1cccc(O)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Oc1cccc(Nc2ncc(C(F)(F)F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9debf532fdeb4000b2f6115e5968094e | CCOC(=O)Cc1ccc(N)cc1.FC(F)(F)c1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCOC(=O)Cc1ccc(Nc2ncc(C(F)(F)F)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.ClC1=NC=C(C(=N1)Cl)C(F)(F)F.NC1=CC=C(C=C1)CC(=O)OCC>>C(C)OC(=O)CC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)CC(=O)OCC)C(F)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:35][cH:36]1.Cl[c:12]1[n:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20](Cl)[n:34]1.Fc1cnc([NH:21][c:25]2[cH:26][c:27]([OH:28])[cH:22][cH:33][cH:32]2)nc1Nc1c[c:30]([OH:29])[cH:31][cH:24][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7... | CCOC(=O)Cc1ccc(N)cc1.FC(F)(F)c1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | CCOC(=O)Cc1ccc(Nc2ncc(C(F)(F)F)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 | null | null | null | Acylation | OtherReaction | 549d2ff1e11d0be5fb33800399fd9792b796eb2d13cf58583e2c068a7dc76d57 | 848aa6ac84a9071da4cd0ad789597c97be76472b2af033c4d066bfa4910ca45d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c;H0;D3;+0:9](-Cl):[#7;a:10]:1.F-c1:c:n:c(-[NH;D2;+0:11]-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16](-[OH;D1;+0:17]):[cH;D2;+0:18]:2):n:c:1-N-c1:[cH;D2;+0:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:[c;H0;D3;+0:22](-[OH;D1;+0:... | null | [] | null | null | null | null | In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-trifluoromethylpyrimidine and ethyl 4-aminophenylacetate were reacted to yield N2,N4-bis[4-(ethoxycarbonylmethyl)phenyl]-5-trifluoromethyl-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.31 (s, 1H), 7.46 (d, 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine | Ester.Secondary amine.Secondary amine | c1cncnc1.c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HF | null | null | null | CCOC(=O)Cc1ccc(N)cc1.FC(F)(F)c1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>CCOC(=O)Cc1ccc(Nc2ncc(C(F)(F)F)c(Nc3ccc(CC(=O)OCC)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0005a79cc674381ab62105fdfec3a9e | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)cc3C)n2)c(C)cc1O | ClC1=NC=C(C(=N1)Cl)F.CC1=C(N)C=C(C(=C1)O)C>>CC1=C(C=C(C(=C1)O)C)NC1=NC=C(C(=N1)NC1=C(C=C(C(=C1)C)O)C)F | [CH3:1][c:2]1[c:3]([NH2:5])[cH:25][c:23]([CH3:24])[c:17]([OH:18])[cH:19]1.Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11](Cl)[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])[cH:19][c:20]3[CH3:21])[n:22]2)[c:23]([CH3:24])[cH:25][c:26]1[OH:27] | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Cl | Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)cc3C)n2)c(C)cc1O | 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:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[O;D1;H1:12]):[c;H0;D3;+0:13](-[C;D1;H3:14]):[cH;D2;+0:15]:[c;H0;D3;+0:16]:1-[NH2;D1;+0:17]>>[C;D1;H3:18]-[c:19]1:[c:20]:[c:21](-[NH;D2;+0:2]-[c;H0;D3;+0:1]2:[#7;a:22]:[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 2,5-dimethyl-4-hydroxyaniline were reacted to yield N2,N4-bis(2,5-dimethyl-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.63 (d, 1H, J=4.2 Hz), 7.05 (s, 1H), 6.97 (s,... | 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 | Cc1cc(O)c(C)cc1N.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2ncc(F)c(Nc3cc(C)c(O)cc3C)n2)c(C)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c11f7f261e494402bcb8ccbfb3b9371b | N#Cc1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>N#Cc1cccc(Nc2ncc(F)c(Nc3cccc(C#N)c3)n2)c1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NC=1C=C(C#N)C=CC1.ClC1=NC=C(C(=N1)Cl)F>>C(#N)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F | c1[c:2]([NH2:1])[cH:6][cH:5][cH:4][c:3]1[C:21]#[N:22].Oc1ccc[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)[cH:23]3)[n:24]2)[cH:25]1>>[N:1]#[C: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]([C:21]#[... | N#Cc1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | N#Cc1cccc(Nc2ncc(F)c(Nc3cccc(C#N)c3)n2)c1 | null | null | null | C-C Coupling | OtherReaction | f9c5cc2c071b0b365cc01379a734d174044a4a98e720c09856f1b393a689b86f | b74a7ddc775509ad4a2c892ea4b99c696bb3caaf018b6e0bf437d25bbaeab0d9 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-c1:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[#7:8]-[c:9](:[#7;a:10]):[#7;a:11]):c:c:c:1.[N;D1;H0:12]#[C;H0;D2;+0:13]-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18](-[NH2;D1;+0:19]):c:1>>[#7;a:10]:[c:9](-[#7:8]-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[c;H0;D3;+0:14](-[C;H0;D2;+0:18]#[... | 76 | [{"value": 76.0, "product": "C(#N)C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 3-aminobenzonitrile (177 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave N2,N4-bis(3-cyanophenyl)-5-fluoro-2,4-pyrimidinediamine (75 mg, 76%). 1H NMR (acetone-d6): δ 7.33 (dt, J=1.8, 7.8 Hz, 1... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Aromatic alcohol.Aromatic alcohol.Primary amine | Nitrile.Nitrile | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | null | null | N#Cc1cccc(N)c1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>N#Cc1cccc(Nc2ncc(F)c(Nc3cccc(C#N)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb8302863d024f0080c9d2ef9a5dfd77 | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(N)C=C1.ClC1=NC=C(C(=N1)Cl)F>>C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)F | F[c:13]1[cH:12][n:11][c:10](Cl)n[c:45]1Cl.[N:14]1([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23][N:33]([c:32]2[cH:31][cH:30][c:29]([NH2:36])[cH:47][cH:46]2)[CH2:34][CH2:35]1.O[c:37]1[cH:24][cH:9][cH:8][c:7]([NH:6][c:5]2[n:4][cH:3][c:2]([F:1])[c:27]([NH:28][c:38]3[cH:39][cH:40][cH:41][c:42](O)[cH:4... | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f64ab4eeeab2901cbfee4b21bf1d2d5c588f1df0df17c9fd013256879da11071 | 093f84d9b74857a6c11654788ba946e281487ddb8d44141c9bac62ff7c98f8c9 | c1ccc(CN2CCN(c3ccc(Nc4ccnc(Nc5ccc(N6CCN(Cc7ccccc7)CC6)cc5)n4)cc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-F):[c;H0;D3;+0:5](-Cl):n:1.O-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:[c:10](-[#7:11]-[c:12]2:[#7;a:13]:[c:14](-[NH;D2;+0:15]-[c;H0;D3;+0:16]3:[c:17]:[c:18]:[c:19]:[c;H0;D3;+0:20](-O):[c:21]:3):[c:22]:[c:23]:[#7;a:24]:2):[cH;D2;+0:25]:1.[NH2;D1;+0:26... | 64 | [{"value": 64.0, "product": "C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 4-(N-benzylpiperazino)aniline (400 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) resulted N2,N4-bis[4-(N-benzylpiperazino)phenyl]-5-fluoro-2,4-pyrimidinediamine (120 mg, 64%). 1H ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Aromatic alcohol.Primary amine.Secondary amine.Tertiary amine.Tertiary amine | Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | c1cncnc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53b4008d8d8b44cda959df4ef21a5728 | Cc1c(N)cccc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Cc1c(O)cccc1Nc1ncc(F)c(Nc2cccc(O)c2C)n1 | OC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.OC=1C(=C(N)C=CC1)C.ClC1=NC=C(C(=N1)Cl)F>>OC=1C(=C(C=CC1)NC1=NC=C(C(=N1)NC1=C(C(=CC=C1)O)C)F)C | [CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[NH2:9].Fc1c(Cl)nc(Cl)n[cH:24]1.Oc1cccc(N[c:10]2[c:13]([F:14])[cH:12][n:11][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:23]3)[n:25]2)c1>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[NH:9][c:10]1[n:11][cH:12][c:13]([F:14])[c:15]([NH:16][c:17]2[cH:18... | Cc1c(N)cccc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | Cc1c(O)cccc1Nc1ncc(F)c(Nc2cccc(O)c2C)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8f652d4d064c3b943686afcd5c7e5fb05e56a93733abb652045aefa93af93e0a | 7dbfc5f6eaf61f7782e3a11ec9b6736dae1500600dba58a0663f40e69cbdff42 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-c1:n:[cH;D2;+0:1]:c(-F):c(-Cl):n:1.O-c1:c:c:c:c(-N-[c;H0;D3;+0:2]2:[#7;a:3]:[c;H0;D3;+0:4](-[#7:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]):[n;H0;D2;+0:12]:[c:13]:[c;H0;D3;+0:14]:2-[F;D1;H0:15]):c:1.[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[CH3;D1;+0:1]-[c;H0;D3;+0:8](:[c:6](-[#7:5]-[c;H0;D3;+0:4]1:[#7;... | 88 | [{"value": 88.0, "product": "OC=1C(=C(C=CC1)NC1=NC=C(C(=N1)NC1=C(C(=CC=C1)O)C)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 3-hydroxy-2-methylaniline (369 mg, 3 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave N2,N4-bis(3-hydroxy-2-methylphenyl)-5-fluoro-2,4-pyrimidinediamine (180 mg, 88%). 1H NMR (acetone-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Primary amine.Secondary amine | Aromatic halide.Secondary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HF | null | null | null | Cc1c(N)cccc1O.Fc1cnc(Cl)nc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1>>Cc1c(O)cccc1Nc1ncc(F)c(Nc2cccc(O)c2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4f7829f72ff4c438bb3b32fd4292992 | Fc1cnc(Cl)nc1Cl.Nc1cccc([N+](=O)[O-])c1>>O=[N+]([O-])c1cccc(Nc2ncc(F)c(Nc3cccc([N+](=O)[O-])c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.[N+](=O)([O-])C=1C=C(N)C=CC1>>[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)[N+](=O)[O-])F | Cl[c:10]1[n:11][cH:12][c:13]([F:14])[c:15](Cl)[n:26]1.[O-:1][N+:2]([c:4]1[cH:25][c:17]([NH2:16])[cH:18][cH:5][cH:27]1)=[O:23]>>[O:1]=[N+: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]([N+:22](=[O:23])[O-:24])[cH:25]3)[n:26]2)[cH:27]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc([N+](=O)[O-])c1 | O=[N+]([O-])c1cccc(Nc2ncc(F)c(Nc3cccc([N+](=O)[O-])c3)n2)c1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 15adb58afbd4a274a49941d5934f1859939f9941608aeae596859d32ae155509 | 4711bb25608d11761d67595f20c50efd0e28c74f4a6353913968b9c28e99f6b2 | 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]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[N+;H0;D3:14](-[O-;H0;D1:15])=[O;H0;D1;+0:16]):[cH;D2;+0:17]:1>>[F;D1;H0:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[#7:18]-[c:19]2:[c:20]:[c:21]:[cH;D2;+0:1... | 76 | [{"value": 76.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.8, "product": "[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (4.7 g, 28.1 mmol) was dissolved in a mixture of MeOH (150 ml) and H2O (15 ml). 3-nitroaniline (15.5 g, 112 mmol) was added and the mixture was refluxed for 20 hours (100° C. oil-bath temperature). The mixture was cooled to 22° C. and filtered. The residue was washed carefully with 200 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitro group.Primary amine | Nitro group.Nitro group.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 100 | null | Fc1cnc(Cl)nc1Cl.Nc1cccc([N+](=O)[O-])c1>O.CO>O=[N+]([O-])c1cccc(Nc2ncc(F)c(Nc3cccc([N+](=O)[O-])c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24b00776d43641aca37ff25252c07a5e | Cc1ccc(N)cc1N.Clc1ccnc(Cl)n1>>Cc1ccc(Nc2ccnc(Nc3ccc(C)c(N)c3)n2)cc1N | ClC1=NC=CC(=N1)Cl.NC=1C=C(N)C=CC1C>>NC=1C=C(C=CC1C)NC1=NC=CC(=N1)NC1=CC(=C(C=C1)C)N | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:22][c:23]1[NH2:24].Cl[c:7]1[n:10][cH:9][cH:8][c:16](Cl)[n:21]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([CH3:17])[c:18]([NH2:19])[cH:20]3)[n:21]2)[cH:22][c:23]1[NH2:24] | Cc1ccc(N)cc1N.Clc1ccnc(Cl)n1 | Cc1ccc(Nc2ccnc(Nc3ccc(C)c(N)c3)n2)cc1N | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | ccced4263878559e35f8e58c96bd0cd951d6c94ea20befe5519837d7566be76b | 2b64964bdfeab4818563f4de0f85c62936d135bbdee525714129037e0a3d7f7a | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:11]-[c:12]1:[n;H0;D2;+0:4]:[c:3]:[cH;D2;+0:2]:[c;H0;D3;+0:5](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[n;H0;D2;+0:6]:1.[C;D1;H3:13]-[c;H0;D3;+0:1](:[c:14]:[c:15]):[c:16](-[N;D1;H2:17]):[c:18] | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloropyrimidine (45 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-amino-4-methylaniline (146 mg, 1.2 mmol) was added and the mixture was refluxed for 20 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and subject... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Primary amine.Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | Cc1ccc(N)cc1N.Clc1ccnc(Cl)n1>O.CO>Cc1ccc(Nc2ccnc(Nc3ccc(C)c(N)c3)n2)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23539d87bdae4874b222c4773e41327b | Cc1ccc(N)cc1N.Fc1cnc(Cl)nc1Cl>>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(N)c3)n2)cc1N | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(N)C=CC1C>>NC=1C=C(C=CC1C)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C)N)F | [cH:1]1[cH:15][c:14]([NH2:13])[cH:23][c:24]([NH2:6])[c:17]1[CH3:18].Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12](Cl)[n:22]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]([NH2:20])[cH:21]3)[n:22]2)[cH:23][c:24]1[NH2:25] | Cc1ccc(N)cc1N.Fc1cnc(Cl)nc1Cl | Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(N)c3)n2)cc1N | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | ca90e3281e5ae2c2a93b6e283a0078d95b57f59d8f3d499d75e811fd45d6f88d | 16fd8e917c81979e1211c135c36b657e44569cc5adf82574e27b1aa93f903756 | 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]):[cH;D2;+0:14]:[c;H0;D3;+0:15]:1-[NH2;D1;+0:16]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c:17]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-amino-4-methylaniline (146 mg, 1.2 mmol) was added and the mixture was refluxed for 20 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Primary amine | Primary amine.Primary amine.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | Cc1ccc(N)cc1N.Fc1cnc(Cl)nc1Cl>O.CO>Cc1ccc(Nc2ncc(F)c(Nc3ccc(C)c(N)c3)n2)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6383bdef7a3d40b3addcae088845728c | Fc1cnc(Cl)nc1Cl.Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1>>Fc1cnc(Nc2ccc(OCc3ccccc3)c(C(F)(F)F)c2)nc1Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C1=CC=CC=C1)OC1=C(C=C(N)C=C1)C(F)(F)F>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OCC1=CC=CC=C1)C(F)(F)F)F)C(F)(F)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:26](Cl)[n:6]1.[cH:7]1[cH:15][cH:14][c:13]([CH2:12][O:11][c:10]2[c:19]([C:20]([F:21])([F:22])[F:42])[cH:24][c:28]([NH2:27])[cH:29][cH:30]2)[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][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]([C:20](... | Fc1cnc(Cl)nc1Cl.Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | Fc1cnc(Nc2ccc(OCc3ccccc3)c(C(F)(F)F)c2)nc1Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 0b52e8f50e855e7c8c513a224a6a68120e65593feb6cb6f05df9ccad6252a828 | f26eb2c2d78d37d2efd07d3d0a8535b3c194cacfe394d7d6eeb3cb1662db753f | c1ccc(COc2ccc(Nc3ccnc(Nc4ccc(OCc5ccccc5)cc4)n3)cc2)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;D1;H0:10])(-[F;H0;D1;+0:11])-[c:12]1:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[NH2;D1;+0:15]):[c:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18]:1-[#8:19]-[C:20]-[c:21]1:[c:22]:[cH;D2;+0:23]:[cH;D2;+0:24]:[cH;D2;+0:25]:[c:26... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 4-benzyloxy-3-trifluoromethylaniline (481 mg, 1.8 mmol) was added and the mixture was refluxed for 2 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced ... | 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.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | O.CO | 70 | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1>O.CO>Fc1cnc(Nc2ccc(OCc3ccccc3)c(C(F)(F)F)c2)nc1Nc1ccc(OCc2ccccc2)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfe7573ff91c4809ba95a1b3fc4dc499 | Fc1cnc(Cl)nc1Cl.N#Cc1cc(N)ccc1O>>N#Cc1cc(Nc2ncc(F)c(Nc3ccc(O)c(C#N)c3)n2)ccc1O | ClC1=NC=C(C(=N1)Cl)F.C(#N)C=1C=C(N)C=CC1O>>OC1=C(C=C(C=C1)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)O)C#N)F)C#N | Cl[c:2]1[n:1][c:7](Cl)[n:8][cH:9][c:10]1[F:11].[c:3]1([C:20]#[N:21])[cH:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1[OH:18]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([OH:18])[c:19]([C:20]#[N:21])[cH:22]3)[n:23]2)[cH:24][cH:25][c:26]1[OH:27] | Fc1cnc(Cl)nc1Cl.N#Cc1cc(N)ccc1O | N#Cc1cc(Nc2ncc(F)c(Nc3ccc(O)c(C#N)c3)n2)ccc1O | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | c56a44963ce552c25d9ee3cd72739f7be391f5544ec2e72748c0f8447b33bceb | edf26fd3cffce9e3f637df3610e1d983a7ab0b28c99c6920d499847f7f934c4d | 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;H0;D3;+0:6]:1-[F;D1;H0:7].[N;D1;H0:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]:[c:15]:[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[#7:18]-[c:19]1:[#7;a:20]:[c;H0;D3;+0:3](-[NH;D2;+0:13]-[c:12]2:[c:14]:[c:15]:[c;H0;D3;+0:16](-[O;D1... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-cyano-4-hydroxyaniline (241 mg, 1.8 mmol) was added and the mixture was refluxed for 2 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Nitrile.Aromatic alcohol.Primary amine | Aromatic halide.Nitrile.Nitrile.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | Fc1cnc(Cl)nc1Cl.N#Cc1cc(N)ccc1O>O.CO>N#Cc1cc(Nc2ncc(F)c(Nc3ccc(O)c(C#N)c3)n2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b2ad25044514d83af1b5fef16e4294f | CC(C)(C)OC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)OC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)OC(C)(C)C)c3)n2)c1 | ClC1=NC=C(C(=N1)Cl)F.C(C)(C)(C)OC(=O)NC=1C=C(N)C=CC1>>C(C)(C)(C)OC(=O)NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)NC(=O)OC(C)(C)C)F | [CH3:1][C:2]([O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([NH2:14])[cH:35]1)([CH3:23])[CH3:28].Cl[c:15]1[n:16][cH:17][c:18]([F:19])[c:20](Cl)[n:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][cH:17][c:18]([F:19])[c:20]([NH:21][c:22]3[cH:23]... | CC(C)(C)OC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl | CC(C)(C)OC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)OC(C)(C)C)c3)n2)c1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | aeadc9ee078c7f067c70e2f26f2cd0977de36baca8478a6e854af9f1131c9fd7 | 3d6b8429061c9abc19c8c22dd7bc1fc94aae8fa6849df816448d62a8bba980d4 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[C;D1;H3:8]-[C;H0;D4;+0:9](-[CH3;D1;+0:10])(-[CH3;D1;+0:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]-[c;H0;D3;+0:16]1:[c:17]:[c:18]:[c:19]:[c;H0;D3;+0:20](-[NH2;D1;+0:21]):[cH;D2;+0:22]:1>>[C:23]-[#8:24]-[C;H0;D3;+0:11](=[O;D1;H0:25])-[#... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (75 mg, 0.45 mmol) was dissolved in a mixture of MeOH (2 ml) and H2O (0.2 ml). 3-tert-butoxycarbonylaminoaniline (374 mg, 1.8 mmol) was added and the mixture was refluxed for 40 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary amine.Boc | Carbamic ester.Ether.Ether.Secondary amine.Secondary amine.Boc.Boc | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | CC(C)(C)OC(=O)Nc1cccc(N)c1.Fc1cnc(Cl)nc1Cl>O.CO>CC(C)(C)OC(=O)Nc1cccc(Nc2ncc(F)c(Nc3cccc(NC(=O)OC(C)(C)C)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-694fface2bbc4a2d8228f77521a87a1b | CC(C)(C)OC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CC(C)(C)OC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)n2)cc1 | ClC1=NC=C(C(=N1)Cl)F.C(C)(C)(C)OC(=O)NC1=CC=C(N)C=C1>>C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)NC(=O)OC(C)(C)C)F | [CH3:1][C:2]([CH3:3])([O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:36][cH:37]1)[CH3:26].Cl[c:14]1[n:15][cH:16][c:17]([F:18])[c:19](Cl)[n:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][c:17]([F:18])[c:19]([NH:20][c:21]3[cH:22][cH:23][... | CC(C)(C)OC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | CC(C)(C)OC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)n2)cc1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 66bea6d05221fb55010294646c0736c76f7f69a68fa88f4af0260c529fa90e63 | 3d6b8429061c9abc19c8c22dd7bc1fc94aae8fa6849df816448d62a8bba980d4 | 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.[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[CH3;D1;+0:15].[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:20].[C:2... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (75 mg, 0.45 mmol) was dissolved in a mixture of MeOH (2 ml) and H2O (0.2 ml). 4-tert-butoxycarbonylaminoaniline (374 mg, 1.8 mmol) was added and the mixture was refluxed for 24 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary amine.Boc | Carbamic ester.Ether.Ether.Secondary amine.Secondary amine.Boc.Boc | c1cncnc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | CC(C)(C)OC(=O)Nc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>O.CO>CC(C)(C)OC(=O)Nc1ccc(Nc2ncc(F)c(Nc3ccc(NC(=O)OC(C)(C)C)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19561014c49148d380cef15fa344df7e | Fc1cnc(Cl)nc1Cl.Nc1ccc([N+](=O)[O-])c(N)c1>>Nc1cc(Nc2ncc(F)c(Nc3ccc([N+](=O)[O-])c(N)c3)n2)ccc1[N+](=O)[O-] | ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(N)C=CC1[N+](=O)[O-]>>NC=1C=C(C=CC1[N+](=O)[O-])NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)[N+](=O)[O-])N)F | Cl[c:6]1[n:7][cH:8][c:9]([F:10])[c:11](Cl)[n:23]1.[NH2:1][c:2]1[cH:3][c:4]([NH2:5])[cH:13][cH:25][c:26]1[N+:27]([O-:18])=[O:28]>>[NH2:1][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]([N+:17](=[O:18])[O-:19])[c:20]([NH2:21])[cH:22]3)[n:23]2)[cH:24][cH:25][c:26]1[N+:27](=[... | Fc1cnc(Cl)nc1Cl.Nc1ccc([N+](=O)[O-])c(N)c1 | Nc1cc(Nc2ncc(F)c(Nc3ccc([N+](=O)[O-])c(N)c3)n2)ccc1[N+](=O)[O-] | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 1065a87481444dc55c3b4d3359ac5e2e477427c40027088291320eb4b14a0379 | 9e66df068a4289be37a5ad7339b78fc1b7c23b5453d55228e599014e35e4b9e3 | 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].[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[N+;H0;D3:13](-[O-;H0;D1:14])=[O;D1;H0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:3](-[NH;D2;+0:8]-[c;H0;D3;+0:9]2:[c:18]:[cH;D2;+0:16]:[c:12](-[N... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-amino-4-nitroaniline (184 mg, 1.2 mmol) was added and the mixture was refluxed for 3 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and su... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitro group.Primary amine | Nitro group.Nitro group.Primary amine.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | Fc1cnc(Cl)nc1Cl.Nc1ccc([N+](=O)[O-])c(N)c1>O.CO>Nc1cc(Nc2ncc(F)c(Nc3ccc([N+](=O)[O-])c(N)c3)n2)ccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f9e325e9d314d76b1ac488c0d0c46a8 | Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.Cl>>Cl.NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F | [NH2:2][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]([NH2:21])[cH:22]3)[n:23]2)[cH:24]1>>[NH2:2][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]([NH2:21])[cH:22]3)[n:23]2)[cH:24]1 | Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | null | null | [] | null | null | null | null | N2,N4-Bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine was treated with 2 equivalents of HCl in dioxane. The volatiles were removed under reduced pressure to give N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine hydrogen chloride salt. LCMS: ret. time: 9.74 min.; purity: 91.3%; MS (m/e): 311.06 (MH+).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | null | O1CCOCC1 | null | null | Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>O1CCOCC1>Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-565620cec14c4915988bf35b30efc16f | Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1>>Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1 | NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)N)F.Cl>>Cl.NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)N)F | [NH2:2][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]([NH2:19])[cH:20][cH:21]3)[n:22]2)[cH:23][cH:24]1>>[NH2:2][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]([NH2:19])[cH:20][cH:21]3)[n:22]2)[cH:23][cH:24]1 | Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1 | Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | null | null | [] | null | null | null | null | N2,N4-Bis(4-aminophenyl)-5-fluoro-2,4-pyrimidinediamine was treated with 2 equivalents of HCl in dioxane. The volatiles were removed under reduced pressure to give N2,N4-bis(4-aminophenyl)-5-fluoro-2,4-pyrimidinediamine Hydrogen Chloride Salt. LCMS: ret. time: 11.15 min.; purity: 100%; MS (m/e): 311.09 (MH+).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | null | O1CCOCC1 | null | null | Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1>O1CCOCC1>Nc1ccc(Nc2ncc(F)c(Nc3ccc(N)cc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77f2294c82c941b0bf338106cbeeab8e | Cc1ccc([N+](=O)[O-])cc1N.Fc1cnc(Cl)nc1Cl>>Cc1ccc([N+](=O)[O-])cc1Nc1ncc(F)c(Nc2cc([N+](=O)[O-])ccc2C)n1 | ClC1=NC=C(C(=N1)Cl)F.CC1=C(N)C=C(C=C1)[N+](=O)[O-]>>CC1=C(C=C(C=C1)[N+](=O)[O-])NC1=NC=C(C(=N1)NC1=C(C=CC(=C1)[N+](=O)[O-])C)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH2:18].Cl[c:12]1[n:11][c:17](Cl)[c:15]([F:16])[cH:14][n:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][c:19]2[cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26][c:27]2[CH3:... | Cc1ccc([N+](=O)[O-])cc1N.Fc1cnc(Cl)nc1Cl | Cc1ccc([N+](=O)[O-])cc1Nc1ncc(F)c(Nc2cc([N+](=O)[O-])ccc2C)n1 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 77f1c763abe5a815a6283cb119358cfea9aac602c97a1b730fd41ad013bbe11b | 32a63857b29420ab4657789df3348b04427f3c68b874217e9384d85ddb4c7cd8 | 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:9](:[c:10]):[c;H0;D3;+0:11](-[NH2;D1;+0:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[F;D1;H0:5]):[c;H0;D3;+0:6](-[NH;D2;+0:12]-[c:15](:[c:16]):... | null | [] | 70 | CELSIUS | null | null | 2,4-Dichloro-5-fluoropyrimidine (33 mg, 0.2 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 2-Methyl-5-nitroaniline (122 mg, 0.8 mmol) was added and the mixture was refluxed for 2 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Nitro group.Secondary amine.Secondary amine | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | null | O.CO | 70 | null | Cc1ccc([N+](=O)[O-])cc1N.Fc1cnc(Cl)nc1Cl>O.CO>Cc1ccc([N+](=O)[O-])cc1Nc1ncc(F)c(Nc2cc([N+](=O)[O-])ccc2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-497644a0803945ea95c5b29553065fe0 | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OC(C)(C)C)c3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.BrCC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)C=NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N=CC(=O)OC(C)(C)C)F | Br[CH2:8][C:6](=[O:5])[O:32][C:33]([CH3:1])([CH3:2])[CH3:29].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][c:27]([NH2:28])[cH:37]3)[n:38]2)[cH:39]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][c:... | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OC(C)(C)C)c3)n2)c1 | null | null | null | C-C Coupling | OtherReaction | b4d015a68c9d27ff6d4f67658d4ca1d5b5785450927b31a443542c9b5ce78af2 | 1c129031a38428b623416f2ebcfc45a03ad4369889dee51b4bde27c4c7a825e8 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:17]-[C;H0;D4;+0:5](-[C;D1;H3:18])(-[C;D1;H3:19])-[O;H0;D2;+0:4]-[C:20](=[O;D1;H0:21])-[CH;D2;+0:7]=[N;H0;D2;+0... | null | [] | null | null | null | null | N2,N4-Bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and tert-butyl bromoacetate were reacted together to give N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 29.34 min.; purity: 97.2%; MS (m/e): 427.07 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine.Primary amine.Boc | Ester.Ester.Substituted imine.Substituted imine.Boc.Boc | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Br- | null | null | null | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OC(C)(C)C)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc4468aa82804d1094eb04e97730891e | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.BrCC(=O)OC(C)(C)C>>NC=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)N=CC(=O)OC(C)(C)C | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][c:27]([NH2:28])[cH:29]3)[n:30]2)[cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][c:14]... | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d74397f1c19b4858a093f2d48dc48ecef9f552d10b795d6c41c1c9dd7e7df6db | ca62ba178eccbfdda8ef9737ef5a514cc0fafcb5029004ad209aecf483fa5ca9 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and tert-butyl bromoacetate were reacted together to give N4-(3-aminophenyl)-N2-(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrim... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Substituted imine | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f46f826ffebb46a9ade4ce3704eb7370 | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2nc(Nc3cccc(N)c3)ncc2F)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.BrCC(=O)OC(C)(C)C>>NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N=CC(=O)OC(C)(C)C)F | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][cH:23][c:24]([NH2:25])[cH:26]3)[n:27][cH:28][c:29]2[F:30])[cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][c:14]([... | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | CC(C)(C)OC(=O)C=Nc1cccc(Nc2nc(Nc3cccc(N)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d74397f1c19b4858a093f2d48dc48ecef9f552d10b795d6c41c1c9dd7e7df6db | ca62ba178eccbfdda8ef9737ef5a514cc0fafcb5029004ad209aecf483fa5ca9 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and tert-butyl bromoacetate were reacted together to give N2-(3-aminophenyl)-N4-(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrim... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Substituted imine | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)OC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CC(C)(C)OC(=O)C=Nc1cccc(Nc2nc(Nc3cccc(N)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-901f846156dc48bbb72473e8709693d5 | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OCC)c3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.BrCC(=O)OCC>>C(C)OC(=O)C=NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N=CC(=O)OCC)F | Br[CH2:27][C:28](=[O:3])[O:30][CH2:31][CH3:32].[cH:1]1[c:8]([NH2:7])[cH:35][c:12]([NH:13][c:14]2[n:15][cH:16][c:17]([F:18])[c:19]([NH:20][c:21]3[cH:22][cH:23][cH:24][c:25]([NH2:26])[cH:33]3)[n:34]2)[cH:11][cH:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[N:7][c:8]1[cH:9][cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][... | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OCC)c3)n2)c1 | null | null | null | C-C Coupling | OtherReaction | 9413dfeac77240a8e6d2d3b3595879fe093fbed008bf1445029616e7e5ff04f9 | 9e9ef8e97098d11906094f86c8a15bda5dd23b32f63d69677586b7f73deb86f4 | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[#8:4]-[C:5].[NH2;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[CH3;D1;+0:12]-[C:17]-[O;H0;D2;+0:3]-[C:18](=[O;D1;H0:19])-[C:20]=[N;H0;D2;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[c:21]:1.[... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and ethyl bromoacetate were reacted together to give N2,N4-bis(3-ethoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine.Primary amine | Ester.Ester.Substituted imine.Substituted imine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Br- | null | null | null | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CCOC(=O)C=Nc1cccc(Nc2ncc(F)c(Nc3cccc(N=CC(=O)OCC)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1271f8717ef4650b77584de2f259b0e | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CCOC(=O)C=Nc1cccc(Nc2nc(N(CC(=O)OCC)c3cccc(N=CC(=O)OCC)c3)ncc2F)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)N)F.BrCC(=O)OCC>>C(C)OC(=O)C=NC=1C=C(C=CC1)N(C1=NC=C(C(=N1)NC1=CC(=CC=C1)N=CC(=O)OCC)F)CC(=O)OCC | Br[CH2:18][C:19](=[O:3])[O:21][CH2:22][CH3:23].[cH:1]1[cH:25][c:24]([NH:17][c:16]2[n:15][c:14]([NH:13][c:12]3[cH:11][cH:10][cH:9][c:8]([NH2:7])[cH:41]3)[c:39]([F:40])[cH:38][n:37]2)[cH:36][c:28]([NH2:29])[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[N:7][c:8]1[cH:9][cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][c:16]([N... | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1 | CCOC(=O)C=Nc1cccc(Nc2nc(N(CC(=O)OCC)c3cccc(N=CC(=O)OCC)c3)ncc2F)c1 | null | null | null | C-C Coupling | OtherReaction | 6b118c2bd13e03028fea37b714354da4262d1da7d1dc5034aec19b9d183bbfbd | c0f4e2eb4ee3046b8e121fc93ccc867e5a448eda91e9b2aa1f8f86905ccdf2fd | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[#8:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9].[NH2;D1;+0:10]-[c:11]1:[c:12]:[c:13](-[NH;D2;+0:14]-[c:15](:[#7;a:16]:[c:17]):[#7;a:18]:[c:19]):[cH;D2;+0:20]:[cH;D2;+0:21]:[cH;D2;+0:22]:1>>[CH3;D1;+0:21]-[C:23]-[O;H0;D2;+0:3]-[C:24](=[O;D1;H0:25])-[C:26]=[N;H0;D2;+0:6]-[c... | null | [] | null | null | null | null | In like manner to the preparation of N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and ethyl bromoacetate were reacted together to give N2,N4-bis(3-ethoxycarbonylmethyleneaminophenyl)-N2-(ethoxycarbonylmethyl)-5-fluoro-2,4-py... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine.Primary amine.Secondary amine | Ester.Ester.Ester.Substituted imine.Substituted imine.Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Br- | null | null | null | CCOC(=O)CBr.Nc1cccc(Nc2ncc(F)c(Nc3cccc(N)c3)n2)c1>>CCOC(=O)C=Nc1cccc(Nc2nc(N(CC(=O)OCC)c3cccc(N=CC(=O)OCC)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5a4b9e82bd046fdbcf5b77de08dc2df | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.OC=1C=C(N)C=CC1.Cl>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]3[c:19]([cH:20]2)[O:21][CH2:22][CH2:23][O:24]3)[n:25]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:2... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | null | null | O.CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | To a solution of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine (0.028 g, 0.1 mmol) in MeOH:H2O (1.8:0.2 mL) was added 3-hydroxyaniline (0.033 g, 0.3 mmol) and heated in a sealed tube at 100° C. for 24 h. The resulting reaction was diluted with H2O (10 mL), acidified with 2N HCl (pH>2), saturated and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | O.CO | 100 | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.Nc1cccc(O)c1>O.CO>Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15315344da074e098e53c2b81e57a160 | Nc1ccc2c(c1)OCCO2.OCc1cccc(Nc2nc(Cl)ncc2F)c1>>OCc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)CO)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)CO)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2.Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[O:19][CH... | Nc1ccc2c(c1)OCCO2.OCc1cccc(Nc2nc(Cl)ncc2F)c1 | OCc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[3-(hydroxymethyl)phenyl]-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[3-(hydroxymethyl)phenyl]-2,4-pyrimidin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Nc1ccc2c(c1)OCCO2.OCc1cccc(Nc2nc(Cl)ncc2F)c1>>OCc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56414c60e62544e2910608bdf9b81d14 | OCc1ccc(Nc2nc(Cl)ncc2F)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Nc1nc(N(c2ccc(CO)cc2)c2ccc3c(c2)OCCO3)ncc1F | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)CO)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)N(C1=NC=C(C(=N1)N)F)C1=CC=C(C=C1)CO | Cl[c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][OH:11])[cH:12][cH:13]2)[c:26]([F:27])[cH:25][n:24]1.Oc1cccc(Nc2ncc(F)c([NH:1][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][CH2:21][CH2:22][O:23]4)n2)c1>>[NH2:1][c:2]1[n:3][c:4]([N:5]([c:6]2[cH:7][cH:8][c:9]([CH2:10][OH:11])[cH:12][cH:13]2)[c:14]2[cH:15][cH:... | OCc1ccc(Nc2nc(Cl)ncc2F)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Nc1nc(N(c2ccc(CO)cc2)c2ccc3c(c2)OCCO3)ncc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a795c07de1a4adad7df30b138624085d342542e3eb9b34634b836ec5f9ba8b6a | 8a896ad418ea6c51df5fda6628910b1cedc756a2f1b66521159b0a137fbd148f | c1ccc(N(c2ccc3c(c2)OCCO3)c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c;H0;D3;+0:8](-[F;D1;H0:9]):[c:10]:[n;H0;D2;+0:11]:1.F-c1:c:n:c(-N-c2:c:c:c:c(-O):c:2):n:c:1-[NH;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]-[#8:18]>>[#8:18]-[c:17]:[c:16]:[c;H0;D3;+0:13](-[N;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;... | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[4-(hydroxymethyl)phenyl]-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[4-(hydroxymethyl)phenyl]-2,4-pyrimidin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Secondary amine.Secondary amine.Secondary amine | Aromatic halide.Primary amine.Tertiary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccccc1.c1ccc2c(c1)OCCO2 | HF | null | null | null | OCc1ccc(Nc2nc(Cl)ncc2F)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Nc1nc(N(c2ccc(CO)cc2)c2ccc3c(c2)OCCO3)ncc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a475d72e64db464c9e23b28c47663076 | OC(CNc1nc(Cl)ncc1F)c1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Nc1nc(N(CC(O)c2ccccc2)c2ccc3c(c2)OCCO3)ncc1F | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NCC(C1=CC=CC=C1)O)F.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)N(C1=NC=C(C(=N1)N)F)CC(C1=CC=CC=C1)O | Fc1c[n:1][c:2](Cl)[n:3][c:4]1[NH:5][CH2:6][CH:7]([OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.Oc1cccc(Nc2nc(N[c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][CH2:23][O:24]4)[c:27]([F:28])[cH:26][n:25]2)c1>>[NH2:1][c:2]1[n:3][c:4]([N:5]([CH2:6][CH:7]([OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15... | OC(CNc1nc(Cl)ncc1F)c1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Nc1nc(N(CC(O)c2ccccc2)c2ccc3c(c2)OCCO3)ncc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a795c07de1a4adad7df30b138624085d342542e3eb9b34634b836ec5f9ba8b6a | 8a896ad418ea6c51df5fda6628910b1cedc756a2f1b66521159b0a137fbd148f | c1ccc(CCN(c2ccc3c(c2)OCCO3)c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-[NH;D2;+0:4]-[C:5]-[C:6]):c(-F):c:[n;H0;D2;+0:7]:1.O-c1:c:c:c:c(-N-c2:[n;H0;D2;+0:8]:[c:9]:[c;H0;D3;+0:10](-[F;D1;H0:11]):c(-N-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]-[#8:17]):n:2):c:1>>[#8:17]-[c:16]:[c:15]:[c;H0;D3;+0:12](-[N;H0;D3;+0:4](-[C:5]-[C:6])-[c;H0;D3;+0:3]1:... | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(2-hydroxy-2-phenylethyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydroxy-2-phenylethyl)-2,4-pyrimidin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol.Secondary amine.Secondary amine.Secondary amine | Aromatic halide.Primary amine.Tertiary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1.c1ccccc1.c1ccc2c(c1)OCCO2 | HF | null | null | null | OC(CNc1nc(Cl)ncc1F)c1ccccc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Nc1nc(N(CC(O)c2ccccc2)c2ccc3c(c2)OCCO3)ncc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2432765963844d468fb398ddc333f7f1 | Fc1cnc(Cl)nc1NC1CCCCC1.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NC1CCCCC1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1CCCCC1)F.C1OC=2C=C(N)C=CC2OC1>>C1(CCCCC1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18]([NH:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[n:17]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[O:13][CH2:14][CH2:15][O:16]2>>[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][CH:20]1[CH2:... | Fc1cnc(Cl)nc1NC1CCCCC1.Nc1ccc2c(c1)OCCO2 | Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NC1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)nc(Nc2ccc3c(c2)OCCO3)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-cyclohexyl-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N4-cyclohexyl-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.C1CCCCC1 | HCl | null | null | null | Fc1cnc(Cl)nc1NC1CCCCC1.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57f49d8749484edea66cb791bed1df2d | Nc1ccc2c(c1)OCCO2.O=C(O)C1CCC(Nc2nc(Cl)ncc2F)CC1>>O=C(O)C1CCC(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)CC1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.C(=O)(O)C1CCC(CC1)NC1=NC(=NC=C1F)Cl.C1OC=2C=C(N)C=CC2OC1>>C(=O)(O)C1CCC(CC1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2 | [NH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2.Cl[c:11]1[n:10][c:9]([NH:8][CH:7]2[CH2:6][CH2:5][CH:4]([C:2](=[O:1])[OH:3])[CH2:28][CH2:27]2)[c:25]([F:26])[cH:24][n:23]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([... | Nc1ccc2c(c1)OCCO2.O=C(O)C1CCC(Nc2nc(Cl)ncc2F)CC1 | O=C(O)C1CCC(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)nc(Nc2ccc3c(c2)OCCO3)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, N4-(4-carboxycyclohexyl)-2-chloro-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N4-(4-carboxycyclohexyl)-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CCCCC1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Nc1ccc2c(c1)OCCO2.O=C(O)C1CCC(Nc2nc(Cl)ncc2F)CC1>>O=C(O)C1CCC(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1695895703d049038a2368c1ee4ceddd | C=CCN.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>C=CCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C=C)N>>C(C=C)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH2:1]=[CH:2][CH2:3][NH2:4].Oc1cccc(N[c:5]2[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[O:18][CH2:19][CH2:20][O:21]4)[n:22]2)c1>>[CH2:1]=[CH:2][CH2:3][NH:4][c:5]1[n:6][cH:7][c:8]([F:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[O:18][CH2:19][CH2:20][O:21]3)[n:22]1 | C=CCN.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | C=CCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)ncn1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[C;D1;H2:6]=[C:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H2:6]=[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and allylamine were reacted to yield N2-allyl-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.71 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | C=CCN.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>C=CCNc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be7b2fd9219449198e50cff5abc0fb3d | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)C1=CC=C(N)C=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)CC | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:26][cH:27]1.Oc1cccc(N[c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][CH2:23][O:24]4)[n:25]2)c1>>[CH3:1][CH2:2][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]... | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | CCc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-ethylaniline were reacted to yield N4-(3,4-ethylenedioxyphenyl)-N2-(4-ethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CCc1ccc(N)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>CCc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c132ef6cd323452cb8736bf979fce80a | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[o:32]1.Oc1cccc(N[c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]4[c:22]([cH:23]3)[O:24][CH2:25][CH2:26][O:27]4)[n:28]2)c1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c... | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3occc3c2)n1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[2-(methoxycarbonyl)benzofur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | COC(=O)c1cc2cc(N)ccc2o1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc5c(c4)OCCO5)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2dd2a57d2194491789528391dd096cc3 | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OC(C)C)F.COC(=O)C=1OC2=C(C1)C=C(C=C2)N>>FC=1C(=NC(=NC1)NC=1C=CC2=C(C=C(O2)C(=O)OC)C1)NC1=CC=C(C=C1)OC(C)C | Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]2)[n:28]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[o:32]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([F:... | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)c1cc2cc(N)ccc2o1 | COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4occc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-[4-(isopropoxy)phenyl]-4-pyrimidineamine and 2-methoxycarbonyl-5-aminobenzofuran were reacted to yield 5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2occc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)c1cc2cc(N)ccc2o1>>COC(=O)c1cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fd056468a1f49ca9caa24657e1e57c1 | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2O1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OC(C)C)F.NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>FC=1C(=NC(=NC1)NC=1C=CC2=C(CC(O2)C(=O)OC)C1)NC1=CC=C(C=C1)OC(C)C | Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]2)[n:28]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[O:32]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]... | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1 | COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)CCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(4-isopropoxyphenyl)-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to yield 5-fluoro-N2-(2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2c(c1)CCO2.c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(C)Oc1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1>>COC(=O)C1Cc2cc(Nc3ncc(F)c(Nc4ccc(OC(C)C)cc4)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-011e8e220aae4165bd279defa862d98d | Nc1ccc(S(=O)(=O)N2CCCC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>O=S(=O)(c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1)N1CCCC1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.N1(CCCC1)S(=O)(=O)C1=CC=C(N)C=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)S(=O)(=O)N1CCCC1 | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:27][cH:28]1)[N:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.Oc1cccc(N[c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]4[c:20]([cH:21]3)[O:22][CH2:23][CH2:24][O:25]4)[n:26]2)c1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11]... | Nc1ccc(S(=O)(=O)N2CCCC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | O=S(=O)(c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1)N1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | O=S(=O)(c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1)N1CCCC1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-(tetrahydro-(1H)-pyrrol-1-ylsulfonyl)aniline were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[4-(tetrahydro-(1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(S(=O)(=O)N2CCCC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>O=S(=O)(c1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fb32c9937eb4902aac13fffca4d9595 | NCCCN1CCN(Cc2c(F)cccc2Cl)CC1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(NCCCN2CCN(Cc3c(F)cccc3Cl)CC2)nc1Nc1ccc2c(c1)OCCO2 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=C(CN2CCN(CC2)CCCN)C(=CC=C1)F>>ClC1=C(CN2CCN(CC2)CCCNC2=NC=C(C(=N2)NC2=CC3=C(C=C2)OCCO3)F)C(=CC=C1)F | [NH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[c:16]([F:17])[cH:18][cH:19][cH:20][c:21]2[Cl:22])[CH2:23][CH2:24]1.Oc1cccc(N[c:5]2[n:4][cH:3][c:2]([F:1])[c:26]([NH:27][c:28]3[cH:29][cH:30][c:31]4[c:32]([cH:33]3)[O:34][CH2:35][CH2:36][O:37]4)[n:25]2)c1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][CH2:7]... | NCCCN1CCN(Cc2c(F)cccc2Cl)CC1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Fc1cnc(NCCCN2CCN(Cc3c(F)cccc3Cl)CC2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(CN2CCN(CCCNc3nccc(Nc4ccc5c(c4)OCCO5)n3)CC2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-[4-(2-chloro-6-fluorobenzyl)piperazino]propylamine were reacted to yield N2-[3-[4-(2-chloro-6-fluorobenzyl)piperazino]propyl]... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | NCCCN1CCN(Cc2c(F)cccc2Cl)CC1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(NCCCN2CCN(Cc3c(F)cccc3Cl)CC2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33ff58fd18774ccca97e965b3054c35f | CC(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>COC(=O)C1Cc2cc(N(c3ccc(C(C)(C)C)cc3)c3ncc(F)c(N)n3)ccc2O1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.C(C)(C)(C)C1=CC=C(C=C1)NC1=NC(=NC=C1F)Cl.NC=1C=CC2=C(CC(O2)C(=O)OC)C1>>C(C)(C)(C)C1=CC=C(C=C1)N(C1=NC=C(C(=N1)N)F)C=1C=CC2=C(CC(O2)C(=O)OC)C1 | Fc1cnc(Cl)nc1N[c:11]1[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([NH2:10])[cH:29][cH:30][c:31]2[O:32]1.Oc1cccc(N[c:21]2[n:22][cH:23][c:24]([F:25])[c:26]([NH:27]c3ccc4c(c3)OCCO4)[n:28]2)c1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[... | CC(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | COC(=O)C1Cc2cc(N(c3ccc(C(C)(C)C)cc3)c3ncc(F)c(N)n3)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 743b5d829c69b67b02253d510fd2a7caf8da228178e39373045aafff0f231254 | 23df810aa4023055a884492a8ba0327f220cd6049d3372fe9258107c6d48cf13 | c1ccc(N(c2ccc3c(c2)CCO3)c2ncccn2)cc1 | Cl-c1:n:c:c(-F):c(-N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):n:1.O-c1:c:c:c:c(-N-[c;H0;D3;+0:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-c3:c:c:c4:c(:c:3)-O-C-C-O-4):[#7;a:12]:2):c:1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[NH2;D1;+0:11]-[c:10]1:[#7;a:12]:[c;H0;D3;+0:6](-[N;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c;... | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, N4-(4-tert-butylphenyl]-2-chloro-5-fluoro-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to yield N2-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxyc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Aromatic alcohol.Primary amine.Secondary amine.Secondary amine.Secondary amine | Primary amine.Tertiary amine | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | c1ccccc1.c1cncnc1 | c1ccc2c(c1)CCO2.c1ccccc1.c1cncnc1 | HF | null | null | null | CC(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.COC(=O)C1Cc2cc(N)ccc2O1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>COC(=O)C1Cc2cc(N(c3ccc(C(C)(C)C)cc3)c3ncc(F)c(N)n3)ccc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f2f6bdd49ca42809b3532568e4265b7 | Fc1cnc(Cl)nc1NCc1csc2ccc(Cl)cc12.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NCc1csc2ccc(Cl)cc12 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NCC1=CSC2=C1C=C(C=C2)Cl)F.C1OC=2C=C(N)C=CC2OC1>>ClC=1C=CC2=C(C(=CS2)CNC2=NC(=NC=C2F)NC2=CC3=C(C=C2)OCCO3)C1 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18]([NH:19][CH2:20][c:21]2[cH:22][s:23][c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][c:30]23)[n:17]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[O:13][CH2:14][CH2:15][O:16]2>>[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:... | Fc1cnc(Cl)nc1NCc1csc2ccc(Cl)cc12.Nc1ccc2c(c1)OCCO2 | Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NCc1csc2ccc(Cl)cc12 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(CNc3ccnc(Nc4ccc5c(c4)OCCO5)n3)csc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[(5-chloro-1-benzothiophen-3-yl)methyl]-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N4-[(5-chloro-1-benzothiophen-3-yl)methyl]-N2-(3,4-ethylenedioxyph... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2sccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1NCc1csc2ccc(Cl)cc12.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Nc2ccc3c(c2)OCCO3)nc1NCc1csc2ccc(Cl)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b12aeb8229dd404084d65f5b11baad1c | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>NC1=NC=C(F)C2(NCCSCc3c(F)cccc3Cl)OCCON12 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NCCSCC1=C(C=CC=C1F)Cl)F.O1CCOC2=C1C=CC(=C2)N>>ClC1=C(CSCCNC23N(C(=NC=C2F)N)OCCO3)C(=CC=C1)F | Cl[c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([NH:8][CH2:9][CH2:10][S:11][CH2:12][c:13]2[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]2[Cl:20])[n:25]1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)[O:21][CH2:22][CH2:23][O:24]4)n2)c1>>[NH2:1][C:2]1=[N:3][CH:4]=[C:5]([F:6])[C:7]2([NH:8][CH2:9][CH2:10][S:11][CH2:12][c:13]3[c:14]([F:15])[cH:16][cH:17]... | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | NC1=NC=C(F)C2(NCCSCc3c(F)cccc3Cl)OCCON12 | null | null | null | Protection | OtherReaction | 4000e4170334495cf431d0b1ba3abb74187f62806508bf8d40b4dc644b5fd982 | 6858c44328b034f4296e17509bc9f06c7ecfc7fef2763960f541c12aea48d9fb | C1=CC2(NCCSCc3ccccc3)OCCON2C=N1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[#7:4]-[C:5]):[c;H0;D3;+0:6](-[F;D1;H0:7]):[cH;D2;+0:8]:[n;H0;D2;+0:9]:1.F-c1:c:n:c(-N-c2:c:c:c:c(-O):c:2):n:c:1-N-c1:c:c:c2:c(:c:1)-[O;H0;D2;+0:10]-[C:11]-[C:12]-[O;H0;D2;+0:13]-2>>[C:5]-[#7:4]-[C;H0;D4;+0:3]12-[O;H0;D2;+0:10]-[C:11]-[C:12]-[O;H0;D2;+0:13]-[N;H0;D3;+0:... | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine and 1,4-benzodioxan-6-amine were reacted to yield N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-N2-(3,4-ethylenedioxy)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Aromatic alcohol.Secondary amine.Secondary amine | Alkenyl halide.Ether.Primary amine.Tertiary amine | c1cncnc1.c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | C1=CC2OCCON2C=N1 | c1ccccc1.C1=CC2OCCON2C=N1 | HF | null | null | null | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>NC1=NC=C(F)C2(NCCSCc3c(F)cccc3Cl)OCCON12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f24cded0a7d4702bca6b07410961705 | NCc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3ccc4c(c3)OCCO4)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.O1CCOC2=C1C=CC(=C2)CN>>O1CCOC2=C1C=CC(=C2)CNC2=NC=C(C(=N2)NC2=CC(=CC=C2)O)F | [NH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[O:19][CH... | NCc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCc3ccc4c(c3)OCCO4)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner analogous to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 2,3-dihydro-1,4-benzodioxin-6-ylmethylamine gave N2-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | NCc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3ccc4c(c3)OCCO4)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33091a2939dc4b6997ed743d42c75472 | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCCSCc3c(F)cccc3Cl)n2)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NCCSCC1=C(C=CC=C1F)Cl)F.NC=1C=C(C=CC1)O>>ClC1=C(CSCCNC2=NC(=NC=C2F)NC2=CC(=CC=C2)O)C(=CC=C1)F | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][CH2:16][S:17][CH2:18][c:19]2[c:20]([F:21])[cH:22][cH:23][cH:24][c:25]2[Cl:26])[n:27]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:28]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][CH2:15][CH2:16][S:17][CH2:18][c:19... | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(NCCSCc3c(F)cccc3Cl)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CSCCNc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine and 3-aminophenol were reacted to yield N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1NCCSCc1c(F)cccc1Cl.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCCSCc3c(F)cccc3Cl)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-befe2a908ad7466a85aa8c79e2a84b92 | Cc1onc(-c2ccccc2)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Cc1onc(-c2ccccc2)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.CC1=C(C(=NO1)C1=CC=CC=C1)N>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C(=NOC1C)C1=CC=CC=C1 | [CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1[NH2:13].Oc1cccc(N[c:14]2[n:15][cH:16][c:17]([F:18])[c:19]([NH:20][c:21]3[cH:22][cH:23][c:24]4[c:25]([cH:26]3)[O:27][CH2:28][CH2:29][O:30]4)[n:31]2)c1>>[CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1[NH:13][c:14]1... | Cc1onc(-c2ccccc2)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Cc1onc(-c2ccccc2)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(-c2nocc2Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[C;D1;H3:6]-[c:7]1:[#8;a:8]:[#7;a:9]:[c:10](-[c:11]):[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#8;a:8]:[#7;a:9]:[c:10](-[c:11]):[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 5-methyl-3-phenyl-4-isoxazolamine were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-phenyl-5-methylisoxazol-4-y... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cnoc1.c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | Cc1onc(-c2ccccc2)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Cc1onc(-c2ccccc2)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55449ea3ca114778bd397001b4a40024 | Cc1noc(C)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Cc1noc(C)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.CC1=NOC(=C1N)C>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C(=NOC1C)C | [CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[NH2:8].Oc1cccc(N[c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]4[c:20]([cH:21]3)[O:22][CH2:23][CH2:24][O:25]4)[n:26]2)c1>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[NH:8][c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:... | Cc1noc(C)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Cc1noc(C)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2cnoc2)n1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#8;a:9]:[c:10](-[C;D1;H3:11]):[c:12]:1-[NH2;D1;+0:13]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#8;a:9]:[c:10](-[C;D1;H3:11]):[c:12]:1-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3,5-dimethyl-4-isoxazolamine were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3,5-dimethylisoxazol-4-yl)-2,4-pyr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cnoc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | Cc1noc(C)c1N.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Cc1noc(C)c1Nc1ncc(F)c(Nc2ccc3c(c2)OCCO3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f17169171f4f4400a742c75b63e5cadd | Nc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2Br)c1>>Oc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2Br)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.BrC=1C(=NC(=NC1)Cl)NC1=CC(=CC=C1)O.C1OC=2C=C(N)C=CC2OC1>>BrC=1C(=NC(=NC1)NC1=CC2=C(C=C1)OCCO2)NC2=CC(=CC=C2)O | [NH2:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][CH2:19][CH2:20][O:21]2.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:26]2)[c:24]([Br:25])[cH:23][n:22]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[O:18][CH2:19][CH2:20][O... | Nc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2Br)c1 | Oc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 5-bromo-2-chloro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield 5-bromo-N2-(3,4-ethylenedioxyphenyl)-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Nc1ccc2c(c1)OCCO2.Oc1cccc(Nc2nc(Cl)ncc2Br)c1>>Oc1cccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4975a6d281b4a70a49cc9a7eb92a6e7 | C=CCN.Oc1cccc(Nc2nc(Cl)ncc2Br)c1>>C=CCNc1ncc(Br)c(Nc2cccc(O)c2)n1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.BrC=1C(=NC(=NC1)Cl)NC1=CC(=CC=C1)O.C(C=C)N>>C(C=C)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)Br | [CH2:1]=[CH:2][CH2:3][NH2:4].Cl[c:5]1[n:6][cH:7][c:8]([Br:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]2)[n:19]1>>[CH2:1]=[CH:2][CH2:3][NH:4][c:5]1[n:6][cH:7][c:8]([Br:9])[c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]2)[n:19]1 | C=CCN.Oc1cccc(Nc2nc(Cl)ncc2Br)c1 | C=CCNc1ncc(Br)c(Nc2cccc(O)c2)n1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H2:6]=[C:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H2:6]=[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 5-bromo-2-chloro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and allylamine were reacted to yield N2-allyl-5-bromo-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.08 (s, 1H), 7.21 (t, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | C=CCN.Oc1cccc(Nc2nc(Cl)ncc2Br)c1>>C=CCNc1ncc(Br)c(Nc2cccc(O)c2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28dd18e2221f40b39244d9466cb66b3a | COC(=O)C(Nc1nc(Cl)ncc1C#N)c1ccccc1.Nc1ccc2c(c1)OCCO2>>COC(=O)C(Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1C#N)c1ccccc1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC(C1=CC=CC=C1)C(=O)OC)C#N.C1OC=2C=C(N)C=CC2OC1>>C(#N)C=1C(=NC(=NC1)NC1=CC2=C(C=C1)OCCO2)NC(C2=CC=CC=C2)C(=O)OC | Cl[c:9]1[n:8][c:7]([NH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:23]([C:24]#[N:25])[cH:22][n:21]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[O:17][CH2:18][CH2:19][O:20]2>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][c:7]1[n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([c... | COC(=O)C(Nc1nc(Cl)ncc1C#N)c1ccccc1.Nc1ccc2c(c1)OCCO2 | COC(=O)C(Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1C#N)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-cyano-N4-(methoxycarbonylbenzyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield 5-cyano-N2-(3,4-ethylenedioxyphenyl)-N4-(methoxycarbonylbenzyl)-2,4-pyrimidinediami... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccccc1 | HCl | null | null | null | COC(=O)C(Nc1nc(Cl)ncc1C#N)c1ccccc1.Nc1ccc2c(c1)OCCO2>>COC(=O)C(Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1C#N)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08b886c4988f40c6a406b9390f9ba946 | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>>CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(C)(C)C(=O)OCC)F.C1OC=2C=C(N)C=CC2OC1>>C(C)OC(=O)C(C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2)(C)C | Cl[c:16]1[n:15][c:14]([NH:13][c:12]2[cH:11][cH:10][c:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:33][cH:32]2)[c:30]([F:31])[cH:29][n:28]1.[NH2:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][CH2:26][O:27]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12... | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2 | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to produce N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-N2-(3,4-ethylenediox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>>CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2275de99e7a240238afff0f7431c2643 | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1>>CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | C(C)OC(=O)C(C1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2)(C)C.CC(C)C[AlH]CC(C)C>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)C(CO)(C)C)F | CCO[C:4]([C:2]([CH3:1])([CH3:3])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][CH2:23][O:24]4)[n:25][cH:26][c:27]2[F:28])[cH:29][cH:30]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:15]3[cH:... | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[c:6])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | In like manner to the preparation of N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[4(2-hydroxy-1,1-dimethylethyl)phenyl]-pyrimidine-2,4-diamine, N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine was reduced with DIBALH to give N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | CCOC(=O)C(C)(C)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1>>CC(C)(CO)c1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b09d9929cac447e1a03cbf1477edf3d8 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NC=C1C=COC1>>Fc1cnc(N=Cc2ccoc2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC=C1COC=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)N=CC1=COC=C1 | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:13]1.[NH2:6][CH:7]=[C:8]1[CH:9]=[CH:10][O:11][CH2:12]1>>[F:1][c:2]1[cH:3][n:4][c:5]([N:6]=[CH:7][c:8]2[cH:9][cH:10][o:11][cH:12]2)[n:13][c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:2... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NC=C1C=COC1 | Fc1cnc(N=Cc2ccoc2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 614209a2dcf74b5cea5a0a5e4c81726c3fea0f4a5f06ad41b6db58ca5468c959 | ac25241c0b2d8353923f4369bc8e4ed6bd553b86c27afe0b8a155e817591eca9 | C(=Nc1nccc(Nc2ccc3c(c2)OCCO3)n1)c1ccoc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[CH;D2;+0:7]=[C;H0;D3;+0:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D2;+0:6]=[CH;D2;+0:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[o;H0;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 3-aminomethylenefurane were reacted to give N4-(3,4-ethylenedioxyphenyl)-N2-(3-furanylmethylene)-5-fluoro-2,4-pyrimidined... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ether | Substituted imine | c1cncnc1.C1=COCC1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NC=C1C=COC1>>Fc1cnc(N=Cc2ccoc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4ee279e4d8e4b8a83e804ec235fe1cf | COc1ccc(OCCN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(OCCNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.COC1=CC=C(C=C1)OCCN>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NCCOC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][NH2:10])[cH:29][cH:30]1.Cl[c:11]1[n:12][cH:13][c:14]([F:15])[c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]3[c:22]([cH:23]2)[O:24][CH2:25][CH2:26][O:27]3)[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][NH:10][c:11]2[n:12][cH:13][c:14]([F:15])[c:16]([NH:... | COc1ccc(OCCN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | COc1ccc(OCCNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(OCCNc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2-(4-methoxyphenyloxy)ethyl amine were reacted to give N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[(4-methoxyphenyloxy)ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | COc1ccc(OCCN)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>COc1ccc(OCCNc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a780cacd566144a180c5652518561159 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccc2c(c1)CCO2>>Fc1cnc(NCc2ccc3c(c2)CCO3)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.O1C2=C(CC1)C=C(C=C2)CN>>O1C2=C(CC1)C=C(C=C2)CNC2=NC=C(C(=N2)NC2=CC1=C(C=C2)OCCO1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[n:17]1.[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][O:16]2>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[CH2:14][CH2:15][O:16]3)[n:17... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccc2c(c1)CCO2 | Fc1cnc(NCc2ccc3c(c2)CCO3)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)OCCO3)nc(NCc2ccc3c(c2)CCO3)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2,3-dihydrobenzo[b]furan-5-ylmethylamine were reacted to give N2-[2,3-dihydrobenzo[b]furan-5-ylmethyl]-N4-(3,4-ethylenedi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)CCO2.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccc2c(c1)CCO2>>Fc1cnc(NCc2ccc3c(c2)CCO3)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d5d296f700d4809b3b9d185a6a0dee4 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCC1COc2ccccc2O1>>Fc1cnc(NCC2COc3ccccc3O2)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.O1C(COC2=C1C=CC=C2)CN>>O1C(COC2=C1C=CC=C2)CNC2=NC=C(C(=N2)NC2=CC1=C(C=C2)OCCO1)F | Cl[c:5]1[n:4][cH:3][c:2]([F:1])[c:19]([NH:20][c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[O:27][CH2:28][CH2:29][O:30]3)[n:18]1.[NH2:6][CH2:7][CH:8]1[CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17]1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6][CH2:7][CH:8]2[CH2:9][O:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[O:17... | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCC1COc2ccccc2O1 | Fc1cnc(NCC2COc3ccccc3O2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(c1)OCC(CNc1nccc(Nc3ccc4c(c3)OCCO4)n1)O2 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8:6]-[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 2,3-dihydro-1,4-benzodioxin-2-ylmethylamine were reacted to give N2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N4-(3,4-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCC1COc2ccccc2O1>>Fc1cnc(NCC2COc3ccccc3O2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbaadbede58945129311bf853cc1d3c5 | NCC1COc2ccccc2O1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCC3COc4ccccc4O3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.O1C(COC2=C1C=CC=C2)CN>>O1C(COC2=C1C=CC=C2)CNC2=NC=C(C(=N2)NC2=CC(=CC=C2)O)F | [NH2:11][CH2:12][CH:13]1[CH2:14][O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[O:22]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][CH:13]3[CH2:14][O:15][c:16]4[cH:17][cH:18][cH:19][cH:2... | NCC1COc2ccccc2O1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCC3COc4ccccc4O3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCC3COc4ccccc4O3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8:6]-[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 2,3-dihydro-1,4-benzodioxin-2-ylmethylamine were reacted to give N2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-5-fluoro-N4-(3-hydro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | NCC1COc2ccccc2O1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCC3COc4ccccc4O3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b2334d4ef764f9098cb47b22892ce9e | Nc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Nc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NC1=CC(=CC=C1)N>>NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:23]1.Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21]2)[n:22]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21]3)[n:22]2)[cH:23]1 | Nc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Nc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3-aminophenyl)-N2-[2-(methoxycarbonyl)-benzofurane-5-yl]-5-fluoro-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 1,3-diaminobenzene were reacted to give N2-(3-aminophenyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. LCMS: ret. time: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Nc1cccc(N)c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Nc1cccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0d021c9c74648c3b43894eb474a7822 | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2c(c1)OCCO2 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC=1C=C2C=CNC2=CC1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC=1C=C2C=CNC2=CC1 | [NH2:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][cH:12][cH:13][c:14]2[cH:15]1.Oc1cccc(N[c:5]2[n:4][cH:3][c:2]([F:1])[c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]4[c:23]([cH:24]3)[O:25][CH2:26][CH2:27][O:28]4)[n:16]2)c1>>[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:... | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3[nH]ccc3c2)n1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 5-aminoindole were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[(1H)-indol-5-yl]-2,4-pyrimidinediamine. LCMS: ret... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc3[nH]ccc3c2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55d6bb70d63241188c71f36a4b993be1 | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3ccc4[nH]ccc4c3)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NC=1C=C2C=CNC2=CC1>>FC=1C(=NC(=NC1)NC=1C=C2C=CNC2=CC1)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][cH:14][c:15]2[nH:16][cH:17][cH:18][c:19]2[cH:20]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:25]2)[c:23]([F:24])[cH:22][n:21]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[nH:16][cH:17][cH:18][c:19]4[cH:20]3)[n:21][cH:22]... | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3ccc4[nH]ccc4c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4[nH]ccc4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 5-aminoindole were reacted to yield 5-fluoro-N4-(3-hydroxyphenyl)-N2-[(1H)-indol-5-yl]-2,4-pyrimidinediamine. LCMS: ret. time: 17.31 mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | Nc1ccc2[nH]ccc2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3ccc4[nH]ccc4c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4eab4349b534459b1db309128e872a9 | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2c(c1)OCCO2 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.NC1=CC=C2C=CNC2=C1>>C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC=C2C=CNC2=C1 | [NH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][nH:13][c:14]2[cH:15]1.Oc1cccc(N[c:5]2[n:4][cH:3][c:2]([F:1])[c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]4[c:23]([cH:24]3)[O:25][CH2:26][CH2:27][O:28]4)[n:16]2)c1>>[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:... | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1cc(Nc2ccc3c(c2)OCCO3)nc(Nc2ccc3cc[nH]c3c2)n1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:11] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 6-aminoindole were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-[(1H)-indol-6-yl]-2,4-pyrimidinediamine. LCMS: ret... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2[nH]ccc2c1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc3cc[nH]c3c2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dae1636fc1d94cf5b5f6b56e96dcb3ef | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3ccc4cc[nH]c4c3)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NC1=CC=C2C=CNC2=C1>>FC=1C(=NC(=NC1)NC1=CC=C2C=CNC2=C1)NC1=CC(=CC=C1)O | [NH2:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][nH:18][c:19]2[cH:20]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:25]2)[c:23]([F:24])[cH:22][n:21]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]4[cH:16][cH:17][nH:18][c:19]4[cH:20]3)[n:21][cH:22]... | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(Nc3ccc4cc[nH]c4c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4cc[nH]c4c3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:11] | null | [] | null | null | null | null | In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 6-aminoindole were reacted to yield 5-fluoro-N4-(3-hydroxyphenyl)-N2-[(1H)-indol-6-yl]-2,4-pyrimidinediamine. LCMS: ret. time: 18.13 mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | Nc1ccc2cc[nH]c2c1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(Nc3ccc4cc[nH]c4c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43ce698a5d384257885d58d158e60f6e | Fc1cnc(Cl)nc1Cl.N#Cc1cccc(N)c1>>N#Cc1cccc(Nc2nc(Cl)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.NC=1C=C(C#N)C=CC1.ClC1=NC=C(C(=N1)Cl)F>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F | Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16].[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:17]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][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]1 | Fc1cnc(Cl)nc1Cl.N#Cc1cccc(N)c1 | N#Cc1cccc(Nc2nc(Cl)ncc2F)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] | 86 | [{"value": 86.0, "product": "ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-aminobenzonitrile (142 mg, 1.2 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave 2-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamine (128 mg, 86%) as a white solid. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.N#Cc1cccc(N)c1>>N#Cc1cccc(Nc2nc(Cl)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b2d4bfa52ab4f0e8cddab2687b44e68 | N#Cc1cccc(Nc2nc(Cl)ncc2F)c1.Nc1cccc(O)c1>>N#Cc1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)C#N)F.NC=1C=C(C=CC1)O>>C(#N)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24]2)[c:22]([F:23])[cH:21][n:20]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]3)[n:20][cH:21][c:22]2[F:23])... | N#Cc1cccc(Nc2nc(Cl)ncc2F)c1.Nc1cccc(O)c1 | N#Cc1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 62.2 | [{"value": 62.0, "product": "C(#N)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "C(#N)C=1C=C(C=CC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-aminobenzonitrile (142 mg, 1.2 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave 2-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamine (128 mg, 86%) as a white solid. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | N#Cc1cccc(Nc2nc(Cl)ncc2F)c1.Nc1cccc(O)c1>>N#Cc1cccc(Nc2nc(Nc3cccc(O)c3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fd83e3262514bffb44af03d9d185440 | NCCc1c[nH]c2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCCc3c[nH]c4ccccc34)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.NCCC1=CNC2=CC=CC=C12>>FC=1C(=NC(=NC1)NCCC1=CNC2=CC=CC=C12)NC1=CC(=CC=C1)O | [NH2:11][CH2:12][CH2:13][c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:27]2)[c:25]([F:26])[cH:24][n:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][CH2:13][c:14]3[cH:15][nH:16][c:17]4[cH:18][cH:19][cH:... | NCCc1c[nH]c2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCCc3c[nH]c4ccccc34)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCCc3c[nH]c4ccccc34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 53 | [{"value": 53.0, "product": "FC=1C(=NC(=NC1)NCCC1=CNC2=CC=CC=C12)NC1=CC(=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.4, "product": "FC=1C(=NC(=NC1)NCCC1=CNC2=CC=CC=C12)NC1=CC(=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (50 mg, 0.21 mmol) and tryptamine (100 mg, 0.62 mmol) gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-[2-(indol-3-yl)ethyl]-2,4-pyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | NCCc1c[nH]c2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCCc3c[nH]c4ccccc34)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd14fcdff65e4a40bcd822c0df64ec6f | Cc1cc(N)cc(C)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)cc(C)c1O | CC1=C(C(=CC(=C1)[N+](=O)[O-])C)O.NC1=CC(=C(C(=C1)C)O)C.NC1=CC(=C(C(=C1)C)O)C.ClC1=NC=C(C(=N1)Cl)F.C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O>>ClC1=NC=C(C(=N1)NC1=CC(=C(C(=C1)C)O)C)F | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:14][c:15]([CH3:16])[c:17]1[OH:18].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][c:15]([CH3:16])[c:17]1[OH:18] | Cc1cc(N)cc(C)c1O.Fc1cnc(Cl)nc1Cl | Cc1cc(Nc2nc(Cl)ncc2F)cc(C)c1O | 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 | Using general hydrogenation conditions, 2,6-dimethyl-4-nitrophenol was reduced to 4-amino-2,6-dimethylphenol. In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 4-amino-2,6-dimethylphenol (823 mg, 6 mmol) and 2,4-dichloro-5-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Cc1cc(N)cc(C)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)cc(C)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26cd5e9de5264fa9b2faf8856c366a86 | Fc1cnc(Cl)nc1Cl.NCc1csc2ccccc12>>Fc1cnc(Cl)nc1NCc1csc2ccccc12 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.S1C=C(C2=C1C=CC=C2)CN.ClC1=NC=C(C(=N1)Cl)F>>S1C=C(C2=C1C=CC=C2)CNC2=NC(=NC=C2F)Cl | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][CH2:10][c:11]1[cH:12][s:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][CH2:10][c:11]1[cH:12][s:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | Fc1cnc(Cl)nc1Cl.NCc1csc2ccccc12 | Fc1cnc(Cl)nc1NCc1csc2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(CNc3ccncn3)csc2c1 | 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].[#16;a:9]:[c:10]:[c:11]-[C:12]-[NH2;D1;+0:13]>>[#16;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] | null | [] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of benzothiophen-3-ylmethylamine (244 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave N4-(benzothiophen-3-ylmethyl)-2-chloro-5-fluoro-4-pyrimidineamine. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2sccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.NCc1csc2ccccc12>>Fc1cnc(Cl)nc1NCc1csc2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7db450639411488ba98f6fc52ed4f8fc | Fc1cnc(Cl)nc1NCc1csc2ccccc12.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCc3csc4ccccc34)n2)c1 | S1C=C(C2=C1C=CC=C2)CNC2=NC(=NC=C2F)Cl.NC=1C=C(C=CC1)O>>S1C=C(C2=C1C=CC=C2)CNC2=NC(=NC=C2F)NC2=CC(=CC=C2)O | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]2[cH:17][s:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[n:25]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:26]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]3[cH:17][s:18][c:19]4[cH:20][cH:21][... | Fc1cnc(Cl)nc1NCc1csc2ccccc12.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(NCc3csc4ccccc34)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(NCc3csc4ccccc34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of benzothiophen-3-ylmethylamine (244 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave N4-(benzothiophen-3-ylmethyl)-2-chloro-5-fluoro-4-pyrimidineamine. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2sccc2c1 | HCl | null | null | null | Fc1cnc(Cl)nc1NCc1csc2ccccc12.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCc3csc4ccccc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-901c889f93764914835181cc2adf78e7 | Fc1cnc(Cl)nc1Cl.NCc1cccnc1>>Fc1cnc(Cl)nc1NCc1cccnc1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.N1=CC(=CC=C1)CN.ClC1=NC=C(C(=N1)Cl)F>>ClC1=NC=C(C(=N1)NCC=1C=NC=CC1)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH: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][CH2:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1 | Fc1cnc(Cl)nc1Cl.NCc1cccnc1 | Fc1cnc(Cl)nc1NCc1cccnc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(CNc2ccncn2)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].[#7;a:9]:[c:10]:[c:11]-[C:12]-[NH2;D1;+0:13]>>[#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] | null | [] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-pyridylmethylamine (162 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) were reacted to give 2-chloro-5-fluoro-N4-(3-pyridylmethyl)-4-pyrimidineamine. Then 2-chloro-5-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.NCc1cccnc1>>Fc1cnc(Cl)nc1NCc1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68f9038d57b5492bb239bda8246406f1 | Fc1cnc(Cl)nc1NCc1cccnc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCc3cccnc3)n2)c1 | ClC1=NC=C(C(=N1)NCC=1C=NC=CC1)F.NC=1C=C(C=CC1)O>>FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NCC=1C=NC=CC1 | Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[n:22]1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:23]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[n:22]2)[cH:23]1 | Fc1cnc(Cl)nc1NCc1cccnc1.Nc1cccc(O)c1 | Oc1cccc(Nc2ncc(F)c(NCc3cccnc3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(NCc3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | 43 | [{"value": 43.0, "product": "FC=1C(=NC(=NC1)NC1=CC(=CC=C1)O)NCC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-pyridylmethylamine (162 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) were reacted to give 2-chloro-5-fluoro-N4-(3-pyridylmethyl)-4-pyrimidineamine. Then 2-chloro-5-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | Fc1cnc(Cl)nc1NCc1cccnc1.Nc1cccc(O)c1>>Oc1cccc(Nc2ncc(F)c(NCc3cccnc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d657dc7fa03148dc9d3b0266ec609b7e | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.NC1=CC(=C(C(=C1)C)O)Cl.ClC1=NC=C(C(=N1)Cl)F>>ClC1=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:14][c:15]([Cl:16])[c:17]1[OH:18].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][c:15]([Cl:16])[c:17]1[OH:18] | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl | Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O | 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 manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 4-amino-2-chloro-6-methylphenol and 2,4-dichloro-5-fluoropyrimidine resulted 2-chloro-N4-(3-chloro-4-hydroxy-5-methylphenyl)-5-fluoro-4-pyrimidineamine. The reaction of 2-chloro-N4-(3-chloro-4-h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Cc1cc(N)cc(Cl)c1O.Fc1cnc(Cl)nc1Cl>>Cc1cc(Nc2nc(Cl)ncc2F)cc(Cl)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b76d1950bbad4cfa8654b21c81db293a | Cc1cc(CN)c(C)o1.Fc1cnc(Cl)nc1Cl>>Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.CC=1OC(=CC1CN)C.ClC1=NC=C(C(=N1)Cl)F>>ClC1=NC=C(C(=N1)NCC1=C(OC(=C1)C)C)F | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH2:6])[c:15]([CH3:16])[o:17]1.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][c:4]([CH2:5][NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][cH:12][c:13]2[F:14])[c:15]([CH3:16])[o:17]1 | Cc1cc(CN)c(C)o1.Fc1cnc(Cl)nc1Cl | Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NCc2ccoc2)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].[#8;a:8]:[c:9]:[c:10]-[C:11]-[NH2;D1;+0:12]>>[#8;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] | null | [] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of (2,5-dimethyl-3-furyl)methylamine (188 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave 2-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccoc1.c1cncnc1 | HCl | null | null | null | Cc1cc(CN)c(C)o1.Fc1cnc(Cl)nc1Cl>>Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4f732021af54f45bdd88d47a9fd4c92 | Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1.Nc1cccc(O)c1>>Cc1cc(CNc2nc(Nc3cccc(O)c3)ncc2F)c(C)o1 | ClC1=NC=C(C(=N1)NCC1=C(OC(=C1)C)C)F.NC=1C=C(C=CC1)O>>CC=1OC(=CC1CNC1=NC(=NC=C1F)NC1=CC(=CC=C1)O)C | Cl[c:9]1[n:8][c:7]([NH:6][CH2:5][c:4]2[cH:3][c:2]([CH3:1])[o:24][c:22]2[CH3:23])[c:20]([F:21])[cH:19][n:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH:6][c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]3)[n:18][cH:19][c:20]2[F:21])[c:22]([C... | Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1.Nc1cccc(O)c1 | Cc1cc(CNc2nc(Nc3cccc(O)c3)ncc2F)c(C)o1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(NCc3ccoc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 51 | [{"value": 51.0, "product": "CC=1OC(=CC1CNC1=NC(=NC=C1F)NC1=CC(=CC=C1)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of (2,5-dimethyl-3-furyl)methylamine (188 mg, 1.5 mmol) and 2,4-dichloro-5-fluoropyrimidine (50 mg, 0.3 mmol) gave 2-chloro-N4-[(2,5-dimethyl-3-furyl)methyl]-5-fluoro-4-pyrimidineam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccoc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Cc1cc(CNc2nc(Cl)ncc2F)c(C)o1.Nc1cccc(O)c1>>Cc1cc(CNc2nc(Nc3cccc(O)c3)ncc2F)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4631e193186d42ef88cfbd753326bb82 | CI.Cc1cc([N+](=O)[O-])cc(C)c1O>>COc1c(C)cc([N+](=O)[O-])cc1C | COC=1C=C(C=CC1C(=O)OC)NC1=NC=C(C(=N1)NC1=CC(=C(C=C1)C(=O)OC)OC)F.CC1=C(C(=CC(=C1)[N+](=O)[O-])C)O.C([O-])([O-])=O.[K+].[K+].IC>>CC1=C(C(=CC(=C1)[N+](=O)[O-])C)OC | I[CH3:1].[OH:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[CH3:13] | CI.Cc1cc([N+](=O)[O-])cc(C)c1O | COc1c(C)cc([N+](=O)[O-])cc1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | In a manner analogous to the preparation of N2,N4-bis[3-methoxy-4-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,6-dimethyl-4-nitrophenol (1.67 g, 10 mmol), potassium carbonate (13 g, 0.1 mol) and iodomethane (2.5 mL, 50 mmol) gave 2,6-dimethyl-1-methoxy-4-nitrobenzene. Hydrogenation of 2,6-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | null | null | null | CI.Cc1cc([N+](=O)[O-])cc(C)c1O>>COc1c(C)cc([N+](=O)[O-])cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aaff6688395d4de9aa145f813c722176 | COc1c(C)cc(N)cc1C.Fc1cnc(Cl)nc1Cl>>COc1c(C)cc(Nc2nc(Cl)ncc2F)cc1C | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.CC=1C=C(N)C=C(C1OC)C.ClC1=NC=C(C(=N1)Cl)F>>ClC1=NC=C(C(=N1)NC1=CC(=C(C(=C1)C)OC)C)F | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([NH2:8])[cH:17][c:18]1[CH3:19].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]1[c:4]([CH3:5])[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]1[CH3:19] | COc1c(C)cc(N)cc1C.Fc1cnc(Cl)nc1Cl | COc1c(C)cc(Nc2nc(Cl)ncc2F)cc1C | 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 manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 3,5-dimethyl-4-methoxyaniline (400 mg, 2.6 mmol) and 2,4-dichloro-5-fluoropyrimidine (200 mg, 1.2 mmol) gave 2-chloro-N4-(3,5-dimethyl-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | COc1c(C)cc(N)cc1C.Fc1cnc(Cl)nc1Cl>>COc1c(C)cc(Nc2nc(Cl)ncc2F)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7492e54cf43a4e938b73e69c1b967303 | Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Nc1ccc2c(c1)OCCO2>>Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1F | C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC(=NC=C1F)Cl.C1OC=2C=C(N)C=CC2OC1>>C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)N)F | Cl[c:4]1[n:3][c:2]([NH:1]c2ccc(N3CCN(Cc4ccccc4)CC3)cc2)[c:18]([F:19])[cH:17][n:16]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][CH2:14][O:15]2>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[O:12][CH2:13][CH2:14][O:15]3)[n:16][cH:17][c:18]1[F:19] | Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Nc1ccc2c(c1)OCCO2 | Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bfafa85e3665b745ae0fb3b03c040adf1da4ed59c853924483db53644d10c859 | fe3a543074fcad697362a8387855d67fc4959632df6c4a911a7e8237ce8c30eb | c1cnc(Nc2ccc3c(c2)OCCO3)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](-[NH;D2;+0:6]-c2:c:c:c(-N3-C-C-N(-C-c4:c:c:c:c:c:4)-C-C-3):c:c:2):[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[NH2;D1;+0:6]-[c:5]1:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c:3]:[c:4]:1 | 127.1 | [{"value": 63.0, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)N)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 127.1, "product": "C1OC=2C=C(C=CC2OC1)NC1=NC=C(C(=N1)N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidineamine, the reaction of N4-[4-(N-benzylpiperazino)phenyl]-2-chloro-5-fluoro-4-pyrimidineamine (50 mg, 0.12 mmol) and 3,4-ethylenedioxyaniline (0.045 mL, 0.36 mmol) gave N4-[4-(N-benzylpiperazino)phenyl)]—N2-(3,4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine.Tertiary amine.Tertiary amine | Primary amine.Secondary amine | c1cncnc1.c1ccccc1.C1CNCCN1.c1ccccc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Nc1ccc2c(c1)OCCO2>>Nc1nc(Nc2ccc3c(c2)OCCO3)ncc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d5b339dbc5249189868cb62a5a719f2 | Cc1cc(CN)c(C)o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Cc1cc(CNc2ncc(F)c(Nc3cccc(O)c3)n2)c(C)o1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.CC=1OC(=CC1CN)C>>CC=1OC(=CC1CNC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F)C | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH2:6])[c:22]([CH3:23])[o:24]1.Cl[c:7]1[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]2)[n:21]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([OH:19])[cH:20]3)[n:21]2)[c:22... | Cc1cc(CN)c(C)o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Cc1cc(CNc2ncc(F)c(Nc3cccc(O)c3)n2)c(C)o1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCc3ccoc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 59 | [{"value": 59.0, "product": "CC=1OC(=CC1CNC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (50 mg, 0.21 mmol) and (2,5-dimethyl-3-furyl)methylamine (80 mg, 0.63 mmol) gave N2-[(2,5-dimethyl-3-furyl)methyl]-5-fluo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccoc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Cc1cc(CN)c(C)o1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Cc1cc(CNc2ncc(F)c(Nc3cccc(O)c3)n2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-525412a5664743668ed34a112f8d703d | Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc2c(c1)OCCO2 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(N)C=C1>>C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [NH2:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[cH:24][cH:25]1.Oc1cccc(N[c:5]2[n:4][cH:3][c:2]([F:1])[c:27]([NH:28][c:29]3[cH:30][cH:31][c:32]4[c:33]([cH:34]3)[O:35][CH2:36][CH2:37][O:38]4)[n:26]2)c1>>[F:1][c:2]1[cH:3][n:4][c:5]([NH:6]... | Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1 | Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc2c(c1)OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e16f312cecc082e7cf1a4839fea54ae5324ba5c5d1f980dae59b86af4b4b90d5 | 1bbf4b49d3dd289c9e0371676472302adfe8366ccc422a8efd44cc7951e30d31 | c1ccc(CN2CCN(c3ccc(Nc4nccc(Nc5ccc6c(c5)OCCO6)n4)cc3)CC2)cc1 | O-c1:c:c:c:c(-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):c:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 33 | [{"value": 33.0, "product": "C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethylendioxyphenyl)-5-fluoro-4-pyrimidineamine (50 mg, 0.18 mmol) and 4-(4-benzylpiperazino)aniline (142 mg, 0.53 mmol) resulted N2-[4-(N-benzylpiperazino)phenyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCCO2 | HO- | null | null | null | Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1.Oc1cccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)c1>>Fc1cnc(Nc2ccc(N3CCN(Cc4ccccc4)CC3)cc2)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d53f6ff0b7384f9c954d793179b3f6dc | NCc1csc2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3csc4ccccc34)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.S1C=C(C2=C1C=CC=C2)CN>>S1C=C(C2=C1C=CC=C2)CNC2=NC=C(C(=N2)NC2=CC(=CC=C2)O)F | [NH2:11][CH2:12][c:13]1[cH:14][s:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:26]2)[c:24]([F:25])[cH:23][n:22]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][s:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]34... | NCc1csc2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCc3csc4ccccc34)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCc3csc4ccccc34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#16;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#16;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 53 | [{"value": 53.0, "product": "S1C=C(C2=C1C=CC=C2)CNC2=NC=C(C(=N2)NC2=CC(=CC=C2)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (50 mg, 0.21 mmol) and benzothiophen-3-ylmethylamine (100 mg, 0.61 mmol) gave N2-(benzothiophen-3-ylmethyl)-5-fluoro-N4-(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2sccc2c1 | HCl | null | null | null | NCc1csc2ccccc12.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3csc4ccccc34)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4cf56fa63e3f45689f7876cbfdabd115 | NCc1cccnc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3cccnc3)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.N1=CC(=CC=C1)CN>>FC=1C(=NC(=NC1)NCC=1C=NC=CC1)NC1=CC(=CC=C1)O | [NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:23]2)[c:21]([F:22])[cH:20][n:19]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][n:17][cH:18]3)[n:19][cH:20][c:21]2[F:22])[cH:23]1 | NCc1cccnc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCc3cccnc3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCc3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 62 | [{"value": 62.0, "product": "FC=1C(=NC(=NC1)NCC=1C=NC=CC1)NC1=CC(=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (50 mg, 0.21 mmol) and 3-pyridylmethylamine (68 mg, 0.63 mmol) gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-pyridylmethyl)-2,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | NCc1cccnc1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3cccnc3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4812c28dfa3449da68c5a6cbcecb135 | NCc1ccccn1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3ccccn3)ncc2F)c1 | C1OC=2C=C(C=CC2OC1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O.ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.N1=C(C=CC=C1)CN>>FC=1C(=NC(=NC1)NCC1=NC=CC=C1)NC1=CC(=CC=C1)O | [NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1.Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:23]2)[c:21]([F:22])[cH:20][n:19]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][n:18]3)[n:19][cH:20][c:21]2[F:22])[cH:23]1 | NCc1ccccn1.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | Oc1cccc(Nc2nc(NCc3ccccn3)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(NCc3ccccn3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]:[c:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 62 | [{"value": 62.0, "product": "FC=1C(=NC(=NC1)NCC1=NC=CC=C1)NC1=CC(=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine (50 mg, 0.21 mmol) and 2-pyridylmethylamine (68 mg, 0.63 mmol) gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-pyridylmethyl)-2,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | NCc1ccccn1.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>Oc1cccc(Nc2nc(NCc3ccccn3)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1ac8497423e4e2c9537c4fc30621462 | COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1.Nc1cccc(O)c1>>COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(OC)c1 | ClC1=NC=C(C(=N1)NC1=CC(=CC(=C1)OC)OC)F.OC=1C=C(N)C=CC1>>COC=1C=C(C=C(C1)OC)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:9]1[n:8][c:7]([NH:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[cH:26][c:23]([O:24][CH3:25])[cH:22]2)[c:20]([F:21])[cH:19][n:18]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]3)[n:18][cH:19][c:20]2[F:2... | COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1.Nc1cccc(O)c1 | COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,5-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine with 3-hydroxyaniline gave N4-(3,5-dimethoxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 18... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1.Nc1cccc(O)c1>>COc1cc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0975b591b198471c9013cc1ce4498b7c | CCOC(=O)c1cc2cccc(N)c2[nH]1.COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1>>CCOC(=O)c1cc2cccc(Nc3ncc(F)c(Nc4cc(OC)cc(OC)c4)n3)c2[nH]1 | ClC1=NC=C(C(=N1)NC1=CC(=CC(=C1)OC)OC)F.C(C)OC(=O)C=1NC2=C(C=CC=C2C1)N>>COC=1C=C(C=C(C1)OC)NC1=NC(=NC=C1F)NC=1C=CC=C2C=C(NC12)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([NH2:13])[c:32]2[nH:33]1.Cl[c:14]1[n:15][cH:16][c:17]([F:18])[c:19]([NH:20][c:21]2[cH:22][c:23]([O:24][CH3:25])[cH:26][c:27]([O:28][CH3:29])[cH:30]2)[n:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([NH:13][... | CCOC(=O)c1cc2cccc(N)c2[nH]1.COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1 | CCOC(=O)c1cc2cccc(Nc3ncc(F)c(Nc4cc(OC)cc(OC)c4)n3)c2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cccc4cc[nH]c34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[#7;a:10]:[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[#7;a:10]:[c:11](:[c:12]):[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:15] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,5-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine with 2-ethoxycarbonyl-7-aminoindole gave N4-(3,5-dimethoxyphenyl)-N2-(2-ethoxycarbonylindol-7-yl)-5-fluoro-2,4-pyrimidinedia... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccc2[nH]ccc2c1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1cc2cccc(N)c2[nH]1.COc1cc(Nc2nc(Cl)ncc2F)cc(OC)c1>>CCOC(=O)c1cc2cccc(Nc3ncc(F)c(Nc4cc(OC)cc(OC)c4)n3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90fb9c8ac5174b64ad83dc34fa230162 | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.COc1ccc(N)cc1OC>>CCOc1ccc(Nc2nc(Nc3ccc(OC)c(OC)c3)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)F.COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)F | Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:28][cH:27]2)[c:25]([F:26])[cH:24][n:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH3:18])[c:... | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.COc1ccc(N)cc1OC | CCOc1ccc(Nc2nc(Nc3ccc(OC)c(OC)c3)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(4-ethoxyphenyl)-5-fluoro-4-pyrimidineamine with 3,4-dimethoxyaniline gave N2-(3,4-dimethoxyphenyl)-N4-(4-ethoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.COc1ccc(N)cc1OC>>CCOc1ccc(Nc2nc(Nc3ccc(OC)c(OC)c3)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3192a41df1684485aa324e9bfc534dab | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1cccc(O)c1>>CCOc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)F.OC=1C=C(N)C=CC1>>C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:25][cH:24]2)[c:22]([F:23])[cH:21][n:20]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]3)[n:20][cH:21][c:... | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1cccc(O)c1 | CCOc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(4-ethoxyphenyl)-5-fluoro-4-pyrimidineamine with 3-hydroxyaniline gave N4-(4-ethoxyphenyl)-N2-(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.79 (d, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1cccc(O)c1>>CCOc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34bb06d852504b98bd75226ca77a14db | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>>CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCC)F.C1OC=2C=C(N)C=CC2OC1>>C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1F)NC1=CC2=C(C=C1)OCCO2 | Cl[c:11]1[n:10][c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:28][cH:27]2)[c:25]([F:26])[cH:24][n:23]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][CH2:21][O:22]2>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]4[c:17]([cH:18]3)[O... | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2 | CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(4-ethoxyphenyl)-5-fluoro-4-pyrimidineamine with 3,4-ethylenedioxyaniline gave N4-(4-ethoxyphenyl)-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCOc1ccc(Nc2nc(Cl)ncc2F)cc1.Nc1ccc2c(c1)OCCO2>>CCOc1ccc(Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a694358e6e9c4273be5d562dd8faa8dd | CCOc1ccc(N)cc1.COc1ccc(Nc2nc(Cl)ncc2F)cc1OC>>CCOc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)OC)F.C(C)OC1=CC=C(N)C=C1>>COC=1C=C(C=CC1OC)NC1=NC(=NC=C1F)NC1=CC=C(C=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:27][cH:28]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH3:21])[c:22]([O:23][CH3:24])[cH:25]2)[n:26]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]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:1... | CCOc1ccc(N)cc1.COc1ccc(Nc2nc(Cl)ncc2F)cc1OC | CCOc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine with 4-ethoxyaniline gave N4-(3,4-dimethoxyphenyl)-N2-(4-ethoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | CCOc1ccc(N)cc1.COc1ccc(Nc2nc(Cl)ncc2F)cc1OC>>CCOc1ccc(Nc2ncc(F)c(Nc3ccc(OC)c(OC)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d02599634cb4332bad035289d4ba51f | COc1ccc(Nc2nc(Cl)ncc2F)cc1OC.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1OC | ClC1=NC=C(C(=N1)NC1=CC(=C(C=C1)OC)OC)F.OC=1C=C(N)C=CC1>>COC=1C=C(C=CC1OC)NC1=NC(=NC=C1F)NC1=CC(=CC=C1)O | Cl[c:10]1[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]2)[c:21]([F:22])[cH:20][n:19]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]3)[n:19][cH:20][c:2... | COc1ccc(Nc2nc(Cl)ncc2F)cc1OC.Nc1cccc(O)c1 | COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine with 3-hydroxyaniline gave N4-(3,4-dimethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(Nc2nc(Cl)ncc2F)cc1OC.Nc1cccc(O)c1>>COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f778441648944a999362df2ad6dedd7 | COc1ccc(N)cc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1OC | ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F.COC=1C=C(N)C=CC1OC>>COC=1C=C(C=CC1OC)NC1=NC=C(C(=N1)NC1=CC(=CC=C1)O)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:23][c:24]1[O:25][CH3:26].Cl[c:8]1[n:9][cH:10][c:11]([F:12])[c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21]2)[n:22]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][cH:18][c:19]([OH:20])[cH:21]... | COc1ccc(N)cc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1 | COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3,4-dimethoxyaniline gave N2-(3,4-dimethoxyphenyl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(N)cc1OC.Oc1cccc(Nc2nc(Cl)ncc2F)c1>>COc1ccc(Nc2ncc(F)c(Nc3cccc(O)c3)n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-298c40e5938a48f996f55b2c892f78a4 | CCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.C(C)OC1=CC=C(N)C=C1>>C(C)OC1=CC=C(C=C1)NC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:27][cH:28]1.Cl[c:9]1[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]2[cH:17][cH:18][c:19]3[c:20]([cH:21]2)[O:22][CH2:23][CH2:24][O:25]3)[n:26]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([F:13])[c:14]([NH:15][c:16]3[cH:17][cH:18][c:1... | CCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | CCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(Nc3ccc4c(c3)OCCO4)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-ethoxyaniline were reacted to yield N2-(4-ethoxyphenyl)-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2>>CCOc1ccc(Nc2ncc(F)c(Nc3ccc4c(c3)OCCO4)n2)cc1 |
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