2-Mercaptoethanol → N-(4-Fluorophenyl)-2-[(2-hydroxyethyl)sulfanyl]pyrimidine-5-carboxamide

Participants

Reaction Steps

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (39 mg, 0.14 mmol) in THF (1 mL) was added β-mercaptoethanol (20 μL, 0.28 mmol) followed by DBU (43 μL, 0.28 mmol). After 15 min the reaction was quenched with 40 mL 1% HCl, resulting in the formation of solids. The solids were collected by filtration and washed with water. The filtrate was extracted with dichloromethane to afford a white solid after concentration. These were combined with the solids isolated from the filtration and passed through a plug of SiO2 using 60% ethyl acetate/hexane to afford a white solid. After trituration with dichloromethane/hexane, 19.3 mg (47% yield) of titled product was obtained. API-MS m/z 294 (MH+), 292 (M−H)−.

Provenance & Evidence