Reaction Steps
In a heavy-walled pressure tube, a mixture of methyl-[3-(1-methylpiperidin-4-yl)benzyl]amine (0.14 g, 0.64 mmol) and 2-chloro-6,7-dimethoxy-5-methyl-1H-quinazolin-4-one (0.155 g, 0.60 mmol) in 4 mL of EtOH, was heated to 120° C. for 5 hours. After solvent removal, the residue was purified by flash chromatography eluting with CH2Cl2:MeOH:NH4OH (94.5:5:0.5), and the above-titled Example H-3 crystallized from CH2Cl2/cyclohexane. mp 155.7–158° C.; IR (KBr) νmax 2933, 1651, 1590 cm−1; 1H NMR (DMSO-d6, 2.49) δ 1.59–1.71 (m, 4H), 1.93 (m, 2H), 2.16 (s, 3H), 2.42 (m, 1 H), 2.60 (s, 3H), 2.82 (m, 2 H), 3.01 (s, 3H), 3.62 (s, 3H), 3.84 (s, 3H), 4.78 (s, 2H), 6.63 (br s, 1H), 7.03 (d, 1H, J=7.44), 7.11–7.13 (m, 2 H), 7.25 (t, 1H, J=7.74), 10.81 (br s, D2O, 1H); 13C NMR (DMSO-d6, 39.50) δ 13.44, 32.94, 35.12, 41.08, 46.09, 51.64, 55.44, 55.65, 59.76, 124.61, 125.32, 125.65, 128.44, 137.54, 146.43; MS (ES+) m/z 437 (M+H); Anal. (C25H32N4O3.0.25H2O)C: calcd, 68.08; found, 68.02; H: calcd, 7.43; found, 7.19; N: calcd, 12.70; found, 12.69.
