Triethylamine → Methyl 2-{4-[(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)ethynyl]phenyl}-2-methylpropanoate

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Reaction Steps

A mixture of Example 72B (17 mg, 0.1 mmol), methyl 2-(4-bromophenyl)-2-methylpropanoate (38 mg, 0.15 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 0.005 mmol), CuI (1 mg, 0.005 mmol), and triethylamine (28 μL, 0.2 mmol) in acetonitrile (500 μL) was heated at 95° C. under nitrogen for 1 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a white solid (16 mg, 45% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 3H), 7.64 (d, J=8.48 Hz, 2H), 7.36 (d, J=8.48 Hz, 2H), 3.61 (s, 3H), 2.60 (s, 3H), 1.52 (s, 6H). MS (ESI) m/z 350 (M+H)+.

Provenance & Evidence