4-(4-Trifluoromethylbenzoyl)benzyl bromide → 3-Methyl-2-[4-(4-trifluoromethylbenzoyl) benzylthio]-thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1291343Notes

Reaction equation

HRID 1291343 reaction equation
[SH:1][C:2]1[N:3]([CH3:12])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[F:13][C:14]([F:32])([F:31])[C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1>C(O)C.O.[OH-].[Na+].O>[CH3:12][N:3]1[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]1[S:1][CH2:25][C:24]1[CH:27]=[CH:28][C:21]([C:19](=[O:20])[C:18]2[CH:29]=[CH:30][C:15]([C:14]([F:13])([F:31])[F:32])=[CH:16][CH:17]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 189191184-(4-Trifluoromethylbenzoyl)benzyl bromideHCID 178481668HCID 178481668, compound

Product 1

HCID 699607443-Methyl-2-[4-(4-trifluoromethylbenzoyl) benzylthio]-thieno[3,2-d]pyrimidin-4(3H)-oneYield 47.8%

Reagents, catalysts & solvents 3

HCID 23719242Sodium hydroxide--water (1/1/1)CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-mercapto-3-methylthieno[3,2-d]-pyrimidin-4(3H)-one (1.0 g) and 1N-sodium hydroxide/water (5.1 mg) in ethanol (10 ml) was added 4-(4-trifluoromethylbenzoyl)benzyl bromide (1.73 g) and the mixture was stirred at 60° C. 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-hexane to provide the title compound as colorless solid (1.11 g).

Workup

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

Sources & evidence

ORD record
ord-f1ac4dbedee2429ea2d46e2d03bcf98c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…