Potassium Carbonate → HCID 69960194, compound

HRID 1291320Notes

Reaction equation

HRID 1291320 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[C:10](O)[S:11][C:5]2=[N:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29](CBr)=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1>CN(C=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:13][O:16][C:3]3[N:4]=[C:5]4[S:11][CH:10]=[CH:9][N:6]4[C:7](=[O:8])[C:2]=3[CH3:1])=[CH:28][CH:27]=2)=[O:25])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 22373682HCID 22373682, compound

Product 1

HCID 69960194HCID 69960194, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-methyl-2-hydroxy-5H-thiazolo [3,2-a]pyrimidin-5-one (365 mg) and potassium carbonate (526 mg) in DMF (10 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (664 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: chloroform=2:1:1) and recrystallized from ethyl acetate to provide the title compound as colorless solid (400 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: chloroform=2:1:1)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d1d0913538d1468ca2c815304b19fb2d
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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