Tert-Butylamine → 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A heterogeneous mixture of tert-butylamine (22.83 mL, 217 mmol) and 2-chloro-8-iodo-3-methylquinazolin-4(3H)-one (700) (4.64 g, 14.48 mmol) in 2 mL of THF in a 100 mL RBF fitted with a reflux condenser was heated in an oil bath at 50° C. for 4 h. The reaction mixture was concentrated under reduced pressure and the brown solid was dissolved in 300 mL of EtOAc, washed sequentially with 10 mL of water, 10 mL of sat. NaHCO3 solution and 10 mL of brine. The organic solution was concentrated. The residue was purified on a silica gel column (25-55% EtOAc in hexanes) to afford 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one (4.64 g, 12.99 mmol, 90% yield) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.12 (1H, dd, J=7.5, 1.3 Hz), 7.93 (1H, dd, J=7.8, 1.2 Hz), 6.89 (1H, t, J=7.6 Hz), 6.02 (1H, s), 3.41 (3H, s), 1.60 (9H, s). m/z (ES, +ve) 358.1 (M+H)+.

Provenance & Evidence