Water → Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Participants

Reaction Steps

A 100 mL round-bottomed flask was charged with ethyl-4-hydroxy-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (6.49 g, 28.4 mmol) in 14 mL POCl3. To the solution was added N,N-diisopropylethylamine (1.2 mL), the reaction mixture was stirred at 80˜90° C. for 2 hours. The mixture was condensed under reduced pressure yielding the dark brown residue. To the residue was added iced water, then diluted with DCM, and saturated aqueous NaHCO3 solution. The separated organic layer was dried over MgSO4. The solvent was removed by a rotavapor providing dark brown oily product (6.76 g, 96%). MS m/z: 246.9 (M+H)+, 248.9 (isotope).

Provenance & Evidence