Butyl vinyl ether → 8-(1-Butoxyvinyl)-2-(1-phenylcyclopropyl)quinazoline

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-2-(1-phenylcyclopropyl)quinazoline (153.8 mg, 0.473 mmol), diacetoxypalladium (10.62 mg, 0.047 mmol), potassium carbonate (131 mg, 0.946 mmol), 1,3-bis(diphenylphosphino)propane (42.9 mg, 0.104 mmol), and 1-(vinyloxy)butane (0.067 mL, 0.520 mmol) in a mixture of DMF (2.0 mL) and water (0.400 mL) was stirred under argon in a sealed tube at 70° C. for 3 d. The mixture was adsorbed onto silica gel (DMF was removed in vacuo). Chromatographic purification (silica gel, 0-30% EtOAc/hexanes) furnished 8-(1-butoxyvinyl)-2-(1-phenylcyclopropyl)quinazoline (100.0 mg, 0.290 mmol, 61% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ ppm 9.21 (1H, s), 8.16 (1H, dd, J=7.4, 1.4 Hz), 7.73 (1H, dd, J=8.0, 1.4 Hz), 7.43-7.52 (2H, m), 7.32-7.40 (2H, m), 7.26-7.31 (2H, m), 5.32 (1H, d, J=2.0 Hz), 4.41 (1H, d, J=2.0 Hz), 3.81 (2H, t, J=6.5 Hz), 1.82-1.94 (4H, m), 1.69-1.80 (2H, m), 1.47-1.51 (2H, m), 0.93-1.03 (3H, m). m/z (ESI, +ve) 345.2 (M+H)+.

Provenance & Evidence