(3-{6-[2-(2-Fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-acetonitrile → {6-[3-(2-Amino-ethyl)-phenyl]-2-methoxy-pyrimidin-4-yl}-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amine

Participants

Reaction Steps

A solution of (3-{6-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-acetonitrile (660 mg, 1.53 mmol) in MeOH (20 mL) and concentrated HCl (2 mL) is degassed by bubbling with Argon gas for 5 minutes, and treated with palladium hydroxide on carbon (0.4 g) at room temperature. The mixture is hydrogenated for 15 h at room temperature under hydrogen balloon, filtered through celite, and concentrated in a rotavap. The residue is diluted with water, basified with NaOH solution, and extracted with EtOAc. The extracts are dried (MgSO4), filtered, and concentrated to afford {6-[3-(2-amino-ethyl)-phenyl]-2-methoxy-pyrimidin-4-yl}-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amine (0.55 g). LCMS: RT=1.85 minutes; MS: 435 (M+H).

Provenance & Evidence