Aminopyrazine → 2-(Trifluoromethyl)imidazo[1,2-a]pyrazine

HRID 1863932

Reaction equation

HRID 1863932 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]([F:15])([F:14])[F:13])=O>C(O)C>[F:13][C:12]([F:15])([F:14])[C:10]1[N:1]=[C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]2[CH:9]=1

Participants

4

Reactant 2

HCID 78747AminopyrazineHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

Product 1

HCID 32313062-(Trifluoromethyl)imidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-aminopyrazine (5.25 g, 55.2 mmol) in ethanol (120 mL) was added 1-bromo-3,3,3-trifluoroacetone (5.73 mL, 55.2 mmol). The reaction was stirred at reflux for 20 h. After evaporation of solvent, the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted three times with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (silica gel, 1:1 ethyl acetate:hexane, then 100% ethyl acetate) to give the title compound as a solid.

Workup

  1. temperatureat reflux for 20 h
  2. customAfter evaporation of solvent
  3. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica gel, 1:1 ethyl acetate

Sources & evidence

ORD record
ord-3b98f66abca04bdbb1b234af0de7d23e
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Linked notes

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