Hydrochloric Acid → 3-({5-[(4-Fluorophenyl)carbamoyl]pyrimidin-2-yl}sulfanyl)benzoic acid

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Reaction Steps

To a solution of 3-mercaptobenzoic acid (83 mg, 0.54 mmol) in THF (2.5 mL) was added potassium tert-butoxide (1 M in THF, 1.1 ML, 1.1 mmol). After 3 min, 2-methane-sulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide was added in one portion and the solution was stirred for 24 h. Water was added, and then the solution was poured into 3% HCl to precipitate the product. The solids were collected by filtration and washed with water. Flash chromatography on SiO2 using a gradient of 5% methanol/dichloromethane to 10% methanol/dichloromethane afforded 15.1 mg (23% yield) of the titled thioether as a white solid. API-MS m/z 370 (MH+), 368 (M−H)−.

Provenance & Evidence