4-(4-Chlorobenzoyl)benzyl bromide → HCID 178434479, compound

HRID 1291247Notes

Reaction equation

HRID 1291247 reaction equation
[K].[SH:2][C:3]1[N:4]([CH3:14])[C:5](=[O:13])[C:6]2[C:11]([CH3:12])=[N:10][NH:9][C:7]=2[N:8]=1.[Cl:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=2)=[O:21])=[CH:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26][S:2][C:3]3[N:4]([CH3:14])[C:5](=[O:13])[C:6]4[C:11]([CH3:12])=[N:10][NH:9][C:7]=4[N:8]=3)=[CH:24][CH:23]=2)=[O:21])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178434481HCID 178434481, compound

Product 1

HCID 178434479HCID 178434479, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-mercapto-3,5-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one potassium (800 mg) in DMF (12 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (1.05 g) and the mixture was stirred at room temperature for 1 hour. This reaction mixture was poured in water and the resulting crystals were collected by filtration, rinsed with water and methanol, and recrystallized from methanol to provide the title compound as colorless solid (1.086 g). 1H-NMR (DMSO-d6) δ: 2.44(3H,s), 3.42(3H,s), 4.60(2H,s), 7.63(2H,d,J=8.6Hz), 7.71(4H,s), 7.75(2H,d,J=8.6Hz), 13.29(1H,brs).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washrinsed with water and methanol
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-652e90bfca814486b26ade0ff7b87808
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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