Water → HCID 90052476, compound

Participants

Reaction Steps

To a solution of 4-(2-chloro-5-iodopyrimidin-4-yl)morpholine (H11, 300 mg), (S)-tert-butyl (1-((3-ethynylphenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (G1, 558 mg), bis(triphenylphosphine)palladium(II) dichloride (32 mg) and copper(I) iodide (9 mg) in N,N-dimethylformamide (5 mL), triethylamine (640 μL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, 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 basic silica gel column chromatography (eluent, 85 to 70% hexane in ethyl acetate) to obtain (S)-tert-butyl (1-((3-((2-chloro-4-morpholinopyrimidin-5-yl)ethynyl)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (L5, 437 mg).

Provenance & Evidence