Ethyl Acetate → tert-butyl ((1S,3R)-3-((2-chloro-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamate

Participants

Reaction Steps

To a solution of 2-chloro-5-iodo-N-propylpyrimidin-4-amine (F1, 78 mg), bis(triphenylphosphine)palladium(II) dichloride (18 mg) and copper(I) iodide (10 mg) in N,N-dimethylformamide (2 mL), triethylamine (181 μL) and tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate (P0, 70 mg) were added at room temperature, and the mixture was stirred at the same temperature for 8 hours. To the reaction mixture, ethyl acetate and saturated aqueous ammonium chloride were added. The organic layer was separated, washed successively with saturated aqueous ammonium chloride, water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 94 to 60% hexane in ethyl acetate) to obtain tert-butyl ((1S,3R)-3-((2-chloro-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (P1, 83 mg).

Provenance & Evidence