Diisopropylamine → HCID 136376393, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (16 mL, 0.12 mol) in anhydrous tetrahydrofuran (100 mL) was cooled to −50° C. and, with stirring, a 1.6 M n-butyl lithium in hexane solution (73 mL, 0.117 mol) was added dropwise. After the completion of the dropwise addition, the mixture was stirred for 10 min. Then, a solution of 4-methylpyrimidine (10 g, 0.11 mol) in anhydrous tetrahydrofuran (10 mL) was added dropwise at −30° C. The mixture was stirred for 0.5 hrs. and the reaction mixture was cooled to −78° C. A solution of N-(3-methylbenzoyl)propyleneimine (19 g, 0.11 mol) in anhydrous tetrahydrofuran (10 mL) was added dropwise. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 2 hrs. The reaction mixture was heated to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate=7:3). Crystallization from isopropyl ether gave the title compound (11 g, yield 49%).

Provenance & Evidence