Sulfoxonium, trimethyl-, iodide (1:1) → 8-Bromo-2-(1-phenylcyclopropyl)quinazoline

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium tert-butoxide (284 mg, 2.532 mmol) and trimethylsulfoxonium iodide (Aldrich; 557 mg, 2.532 mmol) in anhydrous DMSO (6.5 mL) was stirred under argon at 25° C. for 10 min. A solution of 8-bromo-2-(1-phenylvinyl)quinazoline (393.9 mg, 1.266 mmol) in DMSO (10.0 mL) was added (dropwise, over 8 min), and the resulting brown solution was stirred at 25° C. for 30 min. The reaction was diluted with water (20 mL) and 1.0N aq. HCl (1.2 mL), then partitioned between DCM (120 mL) and water (70 mL). The aq. layer was extracted with additional DCM (70 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-40% EtOAc/hexanes) provided 8-bromo-2-(1-phenylcyclopropyl)quinazoline (153.8 mg, 0.473 mmol, 37% yield) as a light-yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 9.18 (1H, s), 8.11 (1H, d, J=7.4 Hz), 7.78 (1H, d, J=8.0 Hz), 7.50 (2H, d, J=7.6 Hz), 7.38 (3H, td, J=7.6, 2.6 Hz), 7.30 (1H, t, J=7.4 Hz), 1.92-1.98 (2H, m), 1.51-1.55 (2H, m). m/z (ESI, +ve) 325.1 (M+H)+.

Provenance & Evidence