Ethyl 5-amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carboxylate → 5-(4-Chloro-phenyl)-6-[4-(2-chloro-pyrimidin-4-yl)-phenyl]-3-methylsulfanyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693559Notes

Reaction equation

HRID 1693559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[N:17]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O:26][C:27]([C:29]1[C:30]([S:41][CH3:42])=[N:31][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:33]=1[NH2:34])=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:27](=[O:26])[C:29]3[C:30]([S:41][CH3:42])=[N:31][N:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:33]=3[N:34]=[C:9]2[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[N:17]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5189818Ethyl 5-amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carboxylateHCID 57897981N-(4-chloro-phenyl)-4-(2-chloro-pyrimidin-4-yl)-benzamide

Product 1

HCID 578980075-(4-Chloro-phenyl)-6-[4-(2-chloro-pyrimidin-4-yl)-phenyl]-3-methylsulfanyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

5-(4-Chloro-phenyl)-6-[4-(2-chloro-pyrimidin-4-yl)-phenyl]-3-methylsulfanyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one is prepared from N-(4-chloro-phenyl)-4-(2-chloro-pyrimidin-4-yl)-benzamide and 5-amino-3-methylsulfanyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester by following a similar procedure as described in example 2. 1H NMR (CDCl3) δ (ppm) 8.68(d, 1H), 8.15(d, 2H), 8.01(d, 2H), 7.63(d, 1H), 7.49(m, 4H), 7.32(m, 3H). 7.11(d, 2H), 2.73(s, 3H). HPLC-MS calculated C28H18Cl2N6OS (M+1+): 557.1. Found: 557.1.

Sources & evidence

ORD record
ord-cbbad11217464af68510445533f2e185
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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