Ammonia → 2-Morpholino-2-(2-(trifluoromethyl)pyrimidin-5-yl)ethanamine

Reaction equation

[N:1]1([CH:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][CH:15]=2)[C:8]#[N:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N>CO.[Ni]>[N:1]1([CH:7]([C:10]2[CH:15]=[N:14][C:13]([C:16]([F:18])([F:17])[F:19])=[N:12][CH:11]=2)[CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Procedure

A mixture of morpholin-4-yl-(2-trifluoromethyl-pyrimidin-5-yl)-acetonitrile (200 mg, 0.735 mmol), Raney-Ni (200 mg), NH3 (aq) (1.5 mL) in MeOH (20 mL) was degassed and purged with Ar and H2 each 3 times. The mixture was stirred at room temperature under H2 (30 psi) for 25 minutes. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to yield the title compound (175 mg, yield: 86%). 1H NMR (CDCl3 400 MHz): δ ppm 8.83 (s, 2H), 3.80-3.61 (m, 4H), 3.44 (t, J=5.2 Hz, 1H), 3.19-2.99 (m, 2H), 2.52-2.35 (m, 4H).