5-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester → 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid

HRID 1693555Notes

Reaction equation

HRID 1693555 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13]CC)=[O:12])=[C:9]([NH2:16])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1)=[O:5])[CH3:2].[Br:23][C:24]1[CH:39]=[CH:38][C:27]([C:28](Cl)=[N:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1>>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]2[N:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:11](=[O:13])[C:10]3[C:6]([C:4]([OH:3])=[O:5])=[N:7][N:8]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:9]=3[N:16]=2)=[CH:38][CH:39]=1.[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:11](=[O:12])[N:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:28]([C:27]3[CH:38]=[CH:39][C:24]([Br:23])=[CH:25][CH:26]=3)=[N:16][C:9]=2[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 578979175-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl esterHCID 57898171HCID 57898171, compound

Product 2

HCID 578979446-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acidHCID 578980116-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester

Procedure

6-(4-Bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid is prepared from 5-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester and 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride by following a similar procedure as described in example 2 except that the reaction mixture is heated at 170° C. in a microwave for 45 min instead of 20 min. the crude product is purified by preparative LC/MS to yield 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid as the major product and 6-(4 bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester (example 341) as by product. Example 340: HPLC-MS calculated C24H14BrClN4O3 (M+1+): 520.0. Found: 520.0. Example 341: 1H NMR (CDCl3) δ (ppm) 8.10(d, 2H), 7.50(t, 2H), 7.41(m, 3H), 7.34 (d, 2H), 7.20(d, 2H), 7.09 (d, 2H), 4.52(q, 2H), 1.45(t, 3H). HPLC-MS calculated C26H18BrClN4O3 (M+1+): 549.0. Found: 549.0.

Workup

  1. customis purified by preparative LC/MS

Sources & evidence

ORD record
ord-fcec7d68d19a44b49bdc82a22268012f
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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