Triethylamine → HCID 86724250, compound

Participants

Reaction Conditions

Reaction Steps

Under argon atmosphere, a mixture of 4,6-dichloropyrimidine (500 mg, 3.36 mmol), 1-(trimethylsilyl)-1-propyne (0.497 mL, 3.36 mmol), tetrabutylammonium fluoride (1 M in THF, 3.36 mL, 3.36 mmol), triethylamine (1.54 mL, 11.1 mmol), tetrakis(triphenylphosphine)palladium(0) (194 mg, 0.168 mmol), copper(I) iodide (192 mg, 1.01 mmol) and toluene (20 mL) was stirred for 9 hours at 60° C. The mixture was cooled down to ambient temperature, and water was added to the mixture. The mixture was extracted with CHCl3, and the organic layer was dried over MgSO4 and filtered. The filtrate was concentrated at reduced pressure, and purification of the residue with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 20%) afforded 4-chloro-6-(prop-1-yn-1-yl)pyrimidine (207 mg).

Provenance & Evidence