Trimethylsilylacetylene → 5-[(Trimethylsilyl)ethynyl]pyrimidine

Participants

Reaction Steps

Dissolve 5-bromopyrimidine (50.0 g, 314.4 mmol) in triethylamine (400 mL), add copper (I) iodide (1.20 g, 6.2 mmol) and stir mixture under nitrogen. After 15 minutes, add trimethylsilyl acetylene (53.3 mL, 377.3 mmol), followed by dichlorobis(triphenylphosphine) palladium (II) (8.82 g, 12.5 mmol) and stir at room temperature. After 3 hours, filter the solution through Celite®, rinsing with ether. Concentrate the filtrate under reduced pressure. Purification by flash chromatography on silica gel eluting first with hexanes (100%), then with hexanes:ethyl acetate (3:1) gives the title compound: 1H NMR (CDCl3) δ 9.10 (s, 1H), 8.77 (s, 2H), 0.27 (s, 9H).

Provenance & Evidence