Dimethylformamide → HCID 18919258, compound

HRID 1291330Notes

Reaction equation

HRID 1291330 reaction equation
[SH:1][C:2]1[N:3]([CH3:14])[C:4](=[O:13])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1.[OH-].[Na+].CN(C=O)C.[Cl:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1>CO.O>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33][S:1][C:2]3[N:3]([CH3:14])[C:4](=[O:13])[C:5]4[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=4[N:7]=3)=[CH:31][CH:30]=2)=[O:28])=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178435037HCID 178435037, compound

Product 1

HCID 18919258HCID 18919258, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-mercapto-3,5,6-trimethylthieno-[2,3-d]pyrimidin-4(3H)-one (1.13 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 (1.425 g).

Workup

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

Sources & evidence

ORD record
ord-75e96d72cc5e4297b9ab5e4e2158bffd
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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