Water → HCID 89782091, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of MeI (1.68 mL, 27.0 mmol), K2CO3 (2.49 g, 18.01 mmol), 8-bromo-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (402a; 3.00 g, 9.00 mmol) in 30 mL THF was fitted with a water cooled reflux condenser and heated to reflux (80° C. oil bath) overnight under N2. Additional 1.5 equiv MeI was added and heating continued. After 2 h, water was added, and the reaction was partitioned between water and EtOAc. The aqueous layer was washed 1× brine, and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(methylthio)-3-phenylquinazolin-4(3H)-one as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (1H, dd, J=7.8, 1.4 Hz), 8.07 (1H, dd, J=7.8, 1.4 Hz), 7.53-7.61 (3H, m), 7.44-7.51 (2H, m), 7.37 (1H, t, J=7.8 Hz), 2.56 (3H, s). m/z (ESI, +ve) 346.9/349.0 (M+H)+.

Provenance & Evidence