3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one → HCID 19934842, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH:7]([N:16]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-])=O)[CH:23]=3)[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>CCOC(C)=O.[Pd]>[NH2:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH2:30][CH2:31][CH3:32])[N:16]([CH:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:25]2=[O:26]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).