Reaction Steps
(S)-1-(4-(7-acetyl-4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (0.106 g, 0.000234 mol) in dry Tetrahydrofuran (2.10 mL, 0.0259 mol) at 0° C. was added 1.0 M of Borane-THF complex in Tetrahydrofuran (0.92 mL) dropwise. The reaction mixture was warmed to room temperature and for 1 hour. The reaction mixture was cooled at 0° C. then about 1 mL 1M HCl dropwise then added 1M NaOH until pH10. The reaction mixture was extracted three times with 10% MeOH in dichloromethane, dried over Magnesium sulfate, filtered, concentrated, was chromatographed through silica gel (12 g, 0-5% MeOH on dichloromethane), and submitted for purification. 1H NMR (400 MHz, DMSO) δ 8.61 (s, 1H), 8.15 (d, J=8.7, 2H), 7.46 (d, J=8.8, 2H), 6.15 (t, J=5.5, 1H), 3.97 (s, 1H), 3.85 (d, J=10.4, 1H), 3.78 (d, J=11.3, 1H), 3.74-3.62 (m, 3H), 3.55 (t, J=11.2, 1H), 3.40 (t, J=13.4, 2H), 3.18-3.05 (m, 2H), 2.85-2.69 (m, 2H), 2.63-2.47 (m, 3H), 2.43 (d, J=9.0, 1H), 1.76 (ddt, J=38.0, 13.8, 7.1, 2H), 1.11 (t, J=7.1, 3H), 1.06 (t, J=7.2, 3H), 0.82 (t, J=7.4, 3H). LC/MS-m/z+439.2 (M+H)+.
