Triethylamine → HCID 89529909, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 500 mg (2.58 mmol) of 5-bromo-2-chloropyrimidine in 10 ml of N,N-dimethylformamide, 397 mg (3.54 mmol) of methyl 4-pentinoate, which was synthesized by the method described in W. D. Wulff et al., Journal of the American Chemical Society, 1988, Vol. 110, pp. 7419-7434, 49 mg (0.26 mmol) of copper iodide, 149 mg (0.129 mmol) of tetrakis(triphenylphosphine)palladium (0) and 5.0 ml of triethylamine were added, and the reaction solution was stirred at 80° C. for 4 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=93/7-75/25 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 347 mg (yield: 60%) of methyl 5-(2-chloropyrimidin-5-yl)-4-pentinoate.

Provenance & Evidence