Water → HCID 90051762, compound

Participants

Reaction Steps

To a suspension of 4-((5-iodo-4-(propylamino)pyrimidin-2-yl)amino)benzonitrile (F25, 289 mg), bis(triphenylphosphine)palladium(II) dichloride (53 mg) and copper(I) iodide (28 mg) in N,N-dimethylformamide (4 mL), triethylamine (322 μL), 4-pentyn-1-ol (304 mg), and tetrakis(triphenylphosphine)palladium(0) (88 mg) were added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and water were added, and the insoluble matter was removed by filtration through Cerite. The organic layer was separated, washed successively with water, saturated aqueous ammonium chloride 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, 90 to 0% hexane in ethyl acetate) to obtain 4-((5-(5-hydroxy-1-pentyn-1-yl)-4-(propylamino)pyrimidin-2-yl)amino)benzonitrile (G11, 195 mg).

Provenance & Evidence