(E)-5-(4-(benzyloxy)styryl)-N-(4-(difluoromethoxy)phenyl)pyrimidin-2-amine → 4-(2-(2-((4-(Difluoromethoxy)phenyl)amino)pyrimidin-5-yl)ethyl)phenol

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Reaction Steps

To a solution of (E)-5-(4-(benzyloxy)styryl)-N-(4-(difluoromethoxy)phenyl)pyrimidin-2-amine (0.04 g, 0.090 mmol) in methanol (5 mL) was added Pd/C (0.03 g, 0.282 mmol) and stirred at room temperature under H2 (1 atom) for 3 h. The reaction mass was filtered through Celite, concentrated and purified by preparative HPLC on a Waters Xbridge C18 column (19×150 mm, 5 μm) using 0-100% mobile phase B (95:5 Acetonitrile:water with 10 mM NH4OAc) in mobile phase A (5:95 Acetonitrile:water with 10 mM NH4OAc) to give 4-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)ethyl)phenol (0.013 g, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.73 (s, 4H), 6.66 (d, J=8.40 Hz, 2H), 6.83-7.35 (m, 5H), 7.71-7.79 (m, 2H), 8.26 (s, 2H), 9.15 (br. s., 1H), 9.55 (s, 1H). LCMS: RT 2.14 min, (M+H)+358.1.

Provenance & Evidence