Methanol → HCID 59239180, compound

Participants

Reaction Conditions

Reaction Steps

Step 2—Synthesis of compound xa: (S)-4-(benzyloxy)-N-(4-(7-isopropyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyrimidin-2-amine (0.186 g, 0.337 mmol) was purged under nitrogen then added 20% Palladium hydroxide on carbon (2:8, Palladium hydroxide:carbon black, 0.14 g) followed by dry Methanol (4.85 mL, 1.20E2 mmol) Acetic acid (0.46 mL, 8.1 mmol) and dry Tetrahydrofuran (4.85 mL, 59.8 mmol) purged with hydrogen, heated at 40° C. and stirred overnight under an atmosphere of hydrogen. The reaction mixture was purged with nitrogen, added celite, filtered through celite, concentrated, chromatographed through silica gel (12 g, 0-10% MeOH in dichloromethane), and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 9.24 (s, 1H), 8.24 (d, J=8.7, 2H), 8.16 (s, 1H), 7.80 (s, 1H), 7.73 (d, J=8.5, 2H), 5.86 (d, J=5.7, 1H), 4.14 (d, J=6.4, 1H), 3.87 (d, J=11.3, 1H), 3.75-3.56 (m, 7H), 3.47-3.39 (m, 2H), 2.88 (dt, J=13.0, 6.5, 1H), 2.74-2.63 (m, 3H), 2.61-2.55 (m, 2H), 2.51 (m, 1H), 1.24 (d, J=6.6, 3H), 1.08 (d, J=6.5, 6H). LC/MS-m/z+462.2 (M+H)+.

Provenance & Evidence