Trimethylsilylacetylene → 5-[(Trimethylsilyl)ethynyl]pyrimidine

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Reaction Steps

Dissolve 5-bromopyrimidine (50.0 g, 314.4 mmol) in triethylamine (400 mL), add copper (1) iodide (1.20 g, 6.2 mmol) and stir mixture under nitrogen. After 15 min., add trimethylsilyl acetylene (53.3 mL, 377.3 mmol), followed by dichlorobis(triphenyl-phosphine) palladium (11) (8.82 g, 12.5 mmol) and stir at RT. After 3 h, 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:EtOAc (3:1) gives the title compound: 1H NMR (300 MHz, CDCl3) δ 9.10 (s, 1H), 8.77 (s, 2H), 0.27 (s, 9H).

Provenance & Evidence