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

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A suspension of tert-butyl 3-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate (A79) (570 mg, 1.00 mmol) and 10% Pd/C (0.600 g) in EtOAc (13 mL) was stirred under a hydrogen atmosphere for 18 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc and the filtrate concentrated in vacuo to give the title compound A80 as a light yellow foam (521 mg, 90%); 1H NMR (300 MHz, d6-DMSO) δ 8.56 (s, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.33 (d, J=8.5 Hz, 2H), 7.28-7.25 (m, 4H), 4.35 (t, J=8.7 Hz, 2H), 3.99 (dd, J=8.4, 6.7 Hz, 2H), 3.77 (m, 3H), 3.70 (brs, 3H), 3.13 (m, 4H), 1.44 (s, 9H). LCMS-B: rt 9.374 min; m/z 571 [M+H]+.

Provenance & Evidence