Ethyl Acetate → (S)-tert-butyl methyl(1-oxo-1-((5-(2-(phenylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)propan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl (1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (L1, 57 mg) and (1S)-(+)-10-camphorsulfonic acid (150 mg) in N-methylpyrrolidone (1 mL), aniline (60 μL) was added at room temperature, and the mixture was stirred at 60° C. for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 50 to 25% hexane in ethyl acetate) to obtain oily (S)-tert-butyl methyl(1-oxo-1-((5-(2-(phenylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)propan-2-yl)carbamate (L2, 52 mg).

Provenance & Evidence