Potassium Carbonate → HCID 18919194, compound

HRID 1291422Notes

Reaction equation

HRID 1291422 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:12])[C:8]([CH3:11])=[CH:9][N:10]=[C:5]2[S:4][C:3]=1O.[C:14](=[O:17])([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30](CBr)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CN(C=O)C>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:14][O:17][C:9]3[N:10]=[C:5]4[S:4][CH:3]=[C:2]([CH3:1])[N:6]4[C:7](=[O:12])[C:8]=3[CH3:11])=[CH:29][CH:28]=2)=[O:26])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 18919246HCID 18919246, compound

Product 1

HCID 18919194HCID 18919194, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dimethyl-2-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one (513 mg) and potassium carbonate (741 mg) in DMF (10 ml) was added 4-(4-fluorobenzoyl)benzyl bromide (782 mg) and the mixture was stirred at 80° C. for 2 hours. This reaction mixture was concentrated and the residue was diluted with water-ethyl acetate and extracted with ethyl acetate. The extract was purified by silica gel column chromatography (hexane: ethyl acetate =2:1) and recrystallized from ethyl acetate to provide the title compound as colorless solid (76 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. additionthe residue was diluted with water-ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customThe extract was purified by silica gel column chromatography (hexane: ethyl acetate =2:1)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee359423a767465480e836b05ba51656
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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