4-Fluoroaniline → N-(4-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxamide

Participants

Reaction Steps

To a solution of potassium tert-butoxide (1 M in THF, 66 mL, 66 mmol) in THF (66 mL) in an ice bath was added 4-fluoroaniline over 1.5 min. The solution was stirred for 1 min, then a solution of 2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (3.745 g, 18.9 mmol) in THF (30 mL) was added via syringe over 4 min. The syringe was washed with 4 mL THF, and the reaction allowed to proceed for 5 min. The reaction was quenched with 1% HCl (450 mL) resulting in a solid precipitate. The solution was filtered, and the solids washed with water. After drying, the solids were triturated with 10% ethyl acetate/hexane to afford 4.0 g (80% yield) of the titled product as a pale yellow solid, which was used in the following preparations.

Provenance & Evidence