Dimethylformamide → 2-[4-(4-Fluorobenzoyl)benzyl]thio-3-methylthieno-[3,2-d]pyrimidin-4(3H)-one

HRID 1291322Notes

Reaction equation

HRID 1291322 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.[OH-].[Na+].CN(C=O)C.[F:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>C(O)C.O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31][S:1][C:2]3[N:3]([CH3:12])[C:4](=[O:11])[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[N:7]=3)=[CH:29][CH:28]=2)=[O:26])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178481668HCID 178481668, compound

Product 1

HCID 189191192-[4-(4-Fluorobenzoyl)benzyl]thio-3-methylthieno-[3,2-d]pyrimidin-4(3H)-oneYield 69.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-mercapto-3-methylthieno[3,2-d]-pyrimidin-4(3H)-one (1.0 g) and sodium hydroxide (205 mg) in 50% ethanol (12 ml)-DMF (20 ml) was added 4-(4-fluorobenzoyl)benzyl bromide (1.48 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 (1.44 g).

Workup

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

Sources & evidence

ORD record
ord-f8385467382a4cf3bb629675538cfecc
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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