Diisopropylamine → HCID 22452599, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (7.9 mL, 0.056 mole) in THF (100 mL) at −78° C. and under argon was added 2.5M n-butylithium (22.5 mL, 0.056 mole) followed, after 5 minutes, by a solution of 2-methylthio-4-methylpyrimidine (5.27 g, 0.376 mole) in THF (20 mL). Upon stirring for 15 min. at -78° C., a solution of N-methoxy-N-methyl-3-trifluoromethylbenzamide (9.63 g, 0.041 mole) in THF (90 mL) was added. The reaction was allowed to warm to 0° C. and then quenched into water (400 mL) and ethyl acetate (400 mL). The layers were separated and the aqueous layer washed with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a solid (11.9 g). Trituration from 10% ether/hexane (100 mL) gave 9.5 g (78%) of the title compound.

Provenance & Evidence