Methyl 3-mercaptopropionate → 3-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]propionic acid methyl ester

Participants

Reaction Steps

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (50 mg, 0.18 mmol) in THF (0.9 mL) was added methyl-3-mercaptopropionate (40 μL, 0.36 mmol) followed by DBU (60 μL, 0.40 mmol). The solution was stirred for 1 h, diluted with 25% ethyl acetate/hexane and passed through a plug of SiO2 washing with 50% ethyl acetate/hexane. The filtrate was concentrated, and the resulting solids triturated with 20% ethyl acetate/hexane to afford 35.1 mg (58% yield) of the titled product as a white solid. ESI-MS m/z 336 (MH+), 334 (M−H)−.

Provenance & Evidence