Ammonia → 6-(Trifluoromethyl)pyrimidin-4-amine

HRID 895143

Reaction equation

HRID 895143 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=1.FC(F)(F)C1N=C[N:17]=C(O)C=1.N>C(#N)C>[NH2:17][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineHCID 178516143HCID 178516143, compound

Product 1

HCID 223857566-(Trifluoromethyl)pyrimidin-4-amineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 4-chloro-6-trifluoromethylpyrimidine (prepared from 6-trifluoromethyl-4-pyrimidinol as described in U.S. Pat. No. 5,714,438) (17.14 g, 93.9 mmol) in acetonitrile (282 ml) was added 25% aqueous ammonia solution (564 ml) and the mixture was stirred at room temperature for 23 h. The mixture was extracted with ethyl acetate (3×1 l), and the combined extracts were dried (MgSO4) and evaporated in vacuo to leave 14.97 g (98%) of the title compound as a white solid: 1H NMR (360 MHz, DMSO-d6) δ 6.80 (1H, s), 7.52 (2H, br s), 8.49 (1H, s).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×1 l)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-0dca8a64aaf84101b3e1c3d483feb455
Source dataset
uspto-grants-2005_07
Patent number
US06914065B2

Linked notes

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