4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 86676021, compound

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Reaction Steps

A solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (3.0 g, 12.89 mmol), tributyl(1-ethoxyvinyl)stannane (4.79 ml, 14.18 mmol) and bis(triphenylphosphine)palladium dichloride (0.452 g, 0.645 mmol) in N,N-dimethylformamide (43 mL) was heated to 70° C. for 1 hour. The mixture was cooled, treated with a solution of KF (1.5 g in 3 mL water) and stirred overnight at room temperature. The mixture was diluted with water and ether and filtered through diatomaceous earth. The layers were separated and the aqueous layer was extracted into ether. The combined extracts were rinsed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (0-20% gradient ethyl acetate in hexane) to provide the title compound. MS ESI(+) m/z 269.0 [M+H]+.

Provenance & Evidence