Trimethylsilylacetylene → HCID 67540580, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-amino-6-chloropyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (1 g, 3.19 mmol) and TMS-acetylene (1.5 g, 15 mmol) in TEA (10 mL) and THF (30 mL) were added PdCl2(PPh3)2 (0.33 g, 0.47 mmol) and CuI (0.1 g, 0.53 mmol) under N2. The mixture was heated to 80° C. for 20 hours. The solvent was removed and the residue was subject to chromatography on silica gel to afford the product 4-(5-Amino-6-trimethylsilanylethynyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.3 g, 25%). 1H NMR (CDCl3, 400 Hz) δ 8.00 (s, 1H), 3.74 (s, 2H), 3.28-3.25 (m, 4H), 3.02-2.99 (m, 4H), 1.20 (s, 9H), 0.00 (s, 9H). MS (ESI+) [M+H]+ 376.

Provenance & Evidence