Dimethylformamide → 2-[4-(4-Chlorobenzoyl)benzyl]thio-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1291331Notes

Reaction equation

HRID 1291331 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:12])=[CH:10][S:11][C:5]=2[N:4]=[C:3]1[SH:13].[OH-].[Na+].CN(C=O)C.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CO.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][S:13][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[C:6]4[C:9]([CH3:12])=[CH:10][S:11][C:5]=4[N:4]=3)=[CH:30][CH:29]=2)=[O:27])=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178431876HCID 178431876, compound

Product 1

HCID 189191282-[4-(4-Chlorobenzoyl)benzyl]thio-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-oneYield 39.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3,5-dimethyl-2-mercaptothieno[2,3-d]pyrimidin-4(3H)-one (1.06 g) and sodium hydroxide (205 mg) in 50% methanol (16 ml)-DMF (4 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (1.69 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 recrystallized from ethyl acetate to provide the title compound as colorless solid (878 mg).

Workup

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

Sources & evidence

ORD record
ord-1a2e708edc094e94b18bee23c363da57
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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