Ammonia → 2-(Morpholin-4-yl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethan-1-amine

HRID 514884Notes

Reaction equation

HRID 514884 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

5

Reactant 2

HCID 222AmmoniaHCID 68364832HCID 68364832, compound

Product 1

HCID 468355732-(Morpholin-4-yl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethan-1-amineYield 86.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

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): δppm 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).

Workup

  1. customwas degassed
  2. custompurged with Ar and H2 each 3 times
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-923e31101a514c4fb0e0cfab94ab85fc
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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