Potassium Carbonate → 7-[4-(4-Methoxybenzoyl)benzyloxy]-3,6-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 1291423Notes

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7](=[O:13])[C:8]([CH3:12])=[C:9]([OH:11])[N:10]=[C:5]2[S:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([CH2:32][O:11][C:9]3[N:10]=[C:5]4[S:4][CH:3]=[C:2]([CH3:1])[N:6]4[C:7](=[O:13])[C:8]=3[CH3:12])=[CH:34][CH:35]=2)=[O:27])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3,6-dimethyl-7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one (537 mg) and potassium carbonate (745 mg) in DMF (10 ml) was added 4-(4-methoxybenzoyl)benzyl bromide (970 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 (106 mg).

Workup

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

Sources & evidence

ORD record: ord-c234e057f5eb4632bb8b7f3465df9828
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753664

Reaction notes

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