Triethylamine → HCID 19827485, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-4-methyl-3-pyrimidin-5-ylpent-1-yne (1 g, 5.7 mmol), prepared as in Stage (2), 2-iodothiophene (1.2 g, 5.7 mmol), triethylamine (2 ml, 14.5 mmol), copper-I-iodide (mg), and bis(triphenylphosphine)palladium-II-chloride (200 mg) were brought together in dry acetonitrile (55 ml) and the mixture was heated at 65° C. under nitrogen. After 1 hour, the mixture was cooled, quenched in dilute aqueous HCl, neutralised with dilute aqueous ammonia and extracted with ether (3×15 ml). The combined organic extracts were washed with dilute aqueous ammonia, water, and brine before being dried over magnesium sulphate and concentrated under reduced pressure to give an oil. Flash chromatography on silica eluting with hexane-ethyl acetate (1:3) gave the title compound as a solid of melting point 113°-14.5° C.

Provenance & Evidence