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

HRID 1482485Notes

Reaction equation

HRID 1482485 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): 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).

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-8ca9fe43688447338b4c251a2e2b0c0d
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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