Triethylamine → HCID 69967398, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methanesulfonic acid 4-(7-{2-[tert-butoxycarbonyl-(tetrahydro-pyran-4-yl)-amino]-ethylamino}-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-3-yl)-3,5-dichloro-phenyl ester (1.5 g, 2.2 mmol) in acetonitrile (5 mL)/triethylamine (1.9 mL) was degassed (3×) by alternately pulling a vacuum followed by repressurization with nitrogen. Trimethylsilylacetylene (0.50 mL, 3.6 mmol), dichlorobis(triphenylphosphine)palladium (65 mg, 0.093 mmol), and copper(I) iodide (42 mg, 0.22 mmol) were added, and the mixture was degassed (3×) again. The mixture was stirred for 4 hours at 65° C., the black mixture was extracted from saturated aqueous sodium bicarbonate with methylene chloride, dried (Na2SO4), filtered through Celite, concentrated under reduced pressure, and then chromatographed (7:3 hexanes/ethyl acetate) to give the product as a light brown foam (1.2 g, 89%): +APcI MS (M+1)+630; 1H NMR (CDCl3) δ: 7.51 (s, 2H), 5.82 (s, 1H), 2.44 (s, 3H), 2.23 (s, 3H), 1.53 (s, 9H), 0.24 (s, 9H).

Provenance & Evidence