3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one → HCID 19934842, compound

Participants

Reaction Steps

A solution of 12.1 g (26.0 mmol) of 3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitro-quinazolin-4(3H)-one dissolved in 250 ml of EtOAc was hydrogenated under atmospheric pressure over three days in the presence of three portions of 1.2 g of 10% Pd/C. added daily. The mixture was filtered through celite and concentrated in vacuo to give an oil. The product was purified by flash chromatography over silica gel eluting with 50% EtOAc/hexanes to give 7.8 g (18.7 mmol) of the amine. 72% yield. 1H-NMR (CDCl3):0.82 (t, 3H, J=7.2 Hz), 1.49 (bm, 2H), 2.61 (t, 2H, J=7.81 Hz), 3.79 (s, 6H), 3.90 (bs, 2H), 6.85 (d, 4H, J=8.8 Hz), 7.08 (dd, 1H, J=2.8, 8.7 Hz), 7.20 (d, 4H, J=8.4 Hz), 7.42 (d, 1H, J=2.7 Hz), 7.47 (d, 1H, J=8.7 Hz).

Provenance & Evidence