Triethylamine → HCID 90039660, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave tube were dissolved 80 mg (0.26 mmol) of (rac)-1-(5-bromopyrimidin-2-yl)-3-ethylhexahydrocyclopenta[d]imidazol-2(1H)-one (Example 1, step 4) in 3 ml DMF. Argon was bubbled through the solution. Ethynylbenzene (57 μl, 53 mg, 0.52 mmol, 2 equiv.), Bis(triphenylphosphine)palladium(II) chloride (9 mg, 0.013 mmol, 0.05 equiv.), copper (I) iodide (1.5 mg, 7.7 μmol, 0.03 equiv.), triphenylphosphine (2.0 mg, 7.7 μmol, 0.03 equiv.) and 107 μl of triethylamine (78 mg, 0.77 mmol, 3 equiv.) were added. The dark brown solution was stirred at 75° C. overnight, adsorbed on silica and purified by flash chromatography (silica gel, 20 g, 0% to 80% EtOAc in heptane gradient) to yield 72.7 mg (85%) of the title compound as a brown solid, MS: m/e=333.3 (M+H+).

Provenance & Evidence