6-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one → 5-(4-Chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1024600Notes

Reaction equation

HRID 1024600 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH3:31][S-:32].[Na+]>CN(C)C=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:9]2[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=[C:8]2[C:5]2[CH:4]=[CH:3][C:2]([S:32][CH3:31])=[CH:7][CH:6]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 20472026-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-oneHCID 4378561Sodium methanethiolate

Product 1

HCID 578993915-(4-Chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (2.50 g, 5.23 mmol) in dry N,N-dimethyl-formamide (20 mL), sodium thiomethoxide (0.55 g, 7.84 mmol) is added and the resulting mixture is stirred at 80° C. After 1.5 h, the reaction mixture is concentrated and the crude product obtained is purified by column chromatography (silica gel, 60-120 mesh) to afford 5-(4-chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customthe crude product obtained
  3. customis purified by column chromatography (silica gel, 60-120 mesh)

Sources & evidence

ORD record
ord-7225c50f8a6a487baae589f14a4f9264
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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