Potassium Carbonate → 4-methyl-3-[2-methyl-4-(2-methyl-thiazol-4-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 2 (530 mg, 1.93 mmol) in N,N-dimethylformamide (2 mL) was added 4-(chloromethyl)-2-methyl-1,3-thiazole HCl (354 mg, 1.93 mmol), potassium carbonate (666 mg, 4.82 mmol) and 18-crown-6 (50 mg). The slurry was heated at 60° C. for three hours. The reaction was returned to ambient temperature and partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a colorless oil. (120 mg, 16% yield). MS (M+H): 386

Provenance & Evidence