Propargyl alcohol → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol

Participants

Reaction Steps

A deoxygenated mixture of 6-(4-bromophenyl)-3-phenylpyrazolo[1,5-a]pyrimidine (2-2, 3.00 g, 8.57 mmol, 1 equiv), propargyl alcohol (1.50 mL, 25.8 mmol, 3.01 equiv), and tetrakis(triphenylphosphine)palladium (0.500 g, 0.433 mmol, 0.050 equiv) in pyrrolidine (50 mL) was heated at reflux for 2.5 hours. The reaction mixture was concentrated, and the residue was suspended in methanol (50 mL) and filtered to give 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]prop-2-yn-1-ol (2-3) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ9.56 (d, 1H, J=2.4 Hz), 9.07 (d, 1H, J=2.2 Hz), 8.82 (s, 1H), 8.18 (br d, 2H, J=7.8 Hz), 7.92 (d, 2H, J=8.2 Hz), 7.58 (d, 2H, J=8.2 Hz), 7.46 (t, 2H, J=7.8 Hz), 7.27 (t, 1H, J=7.8 Hz), 5.37 (t, 1H, J=6.0 Hz), 4.35 (d, 2H, J=6.0 Hz).

Provenance & Evidence