4-(Trifluoromethyl)benzenecarboximidamide → 4-Methyl-2-(4-trifluoromethylphenyl)pyrimidine

HRID 1077833Notes

Reaction equation

HRID 1077833 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.C[O-].[Na+]>>[CH3:5][C:4]1[CH:3]=[CH:2][N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:4][CH:5]=2)[N:8]=1

Participants

3

Reactant 2

HCID 27773904-(Trifluoromethyl)benzenecarboximidamideHCID 10942334Sodium Methoxide

Product 1

HCID 194302744-Methyl-2-(4-trifluoromethylphenyl)pyrimidineYield 45.6%

Procedure

To a solution of 4-trifluoromethylbenzamidine (45 g) was added sodium methoxide (11.9 g) as a solid in portions, followed by acetylaldehyde dimethylacetal (34.3 g). The mixture was refluxed overnight, then filtered, the solvent evaporated from the filtrate under reduced pressure, and the residue was partitioned between methylene chloride and water, the organic layer separated, washed with brine, dried over sodium sulfate, the solvent evaporated under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 20% ethyl acetate in heptane, to yield 13 g of 4-methyl-2-(4-trifluoromethylphenyl)pyrimidine m.p. 50° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationfiltered
  3. customthe solvent evaporated from the filtrate under reduced pressure
  4. customthe residue was partitioned between methylene chloride and water
  5. customthe organic layer separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent evaporated under reduced pressure
  9. customthe residue flash-chromatographed on silica gel
  10. washeluting with 20% ethyl acetate in heptane

Sources & evidence

ORD record
ord-0862f09b417542958d5b643c857b560e
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Reaction notes

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