Tert-butyl 4-(3-methoxy-4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate → tert-Butyl 4-(3-methoxy-4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate

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Reaction Steps

To a solution of tert-butyl 4-(3-methoxy-4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (I5) (0.358 g, 0.572 mmol) in ethyl acetate (25 mL) and dimethylformamide (5 mL) was added 10% Pd/C (0.200 g). The mixture was evacuated and backfilled three times with hydrogen gas then stirred under a hydrogen atmosphere for 18 hours. The reaction mixture was filtered through a plug of Celite, washing with ethyl acetate then the filtrate was evaporated in vacuo and dried under high vacuum to give the title compound (I6) (0.360 g, 100%) as a viscous yellow oil; 1H NMR (300 MHz, CDCl3) δ 1.48 (s, 9H), 3.00-3.20 (m, 8H), 3.59 (t, 4H, J=4.8 Hz), 3.67 (s, 3H), 3.75 (s, 2H), 3.90 (s, 3H), 6.55-6.57 (m, 2H), 7.19-7.26 (m, 4H), 7.75 (s, 1H), 8.26 (d, 1H, J=9.4 Hz) and 8.50 (s, 1H). LCMS Method B: rt 6.55 min; m/z 630.5 [M+H]+.

Provenance & Evidence