HCID 58222542, compound → HCID 52916786, compound

Participants

Reaction Steps

To a solution of (S)-6-(benzyloxy)-N-(4-(8-cyclopropyl-9-ethyl-6-(3-methylmorpholino)-9H-purin-2-yl)phenyl)pyridin-2-amine (100 mg, 1.78 mmol) in anhydrous MeOH (4 mL) and EtOAc (4 mL) was added 20 wt % Pd(OH)2 on carbon (10.0 mg). The reaction mixture was evacuated with vacuum and purged with H2 (3×), then stirred under an atmosphere of H2 for 2 hours. The reaction mixture was then filtered through a pad of Celite®. The filtrate was concentrated in vacuo and the crude was purified by column chromotagraphy (Si-PPC, gradient 0 to 30% methanol in dichloromethane). Crystallization from ether-heptane afforded the title compound (x-1) (8.6 mg, 10.2%) as a solid. 1H NMR (DMSO-d6, 500 MHz) δ ppm 10.16 (broad s, 1H), 9.05 (broad s, 1H), 8.27 (d, J=8.7 Hz, 2H), 7.76 (broad s, 2H), 7.41 (t, J=7.9 Hz, 1H), 6.29 (broad s, 1H), 5.98 (d, J=6.3 Hz, 1H), 5.36 (broad s, 1H), 5.06 (broad s, 1H), 4.36 (q, J=7.2 Hz, 2H), 3.98 (d, J=8.5 Hz, 1H), 3.78 (d, J=11.2 Hz, 1H), 3.69 (d, J=8.7 Hz, 1H), 3.54 (t, J=10.6 Hz, 1H), 3.44 to 3.33 (m, 1H), 2.30 to 2.19 (m, 1H), 1.40 (t, J=7.1 Hz, 3H), 1.29 (d, J=6.7 Hz, 3H), 1.12 to 0.93 (m, 4H); LC-MS m/z (method C)=472.2 [M+H]+, RT=4.93 min.

Provenance & Evidence