Benzamidine → 4-Amino-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidine-5-carbonitrile

HRID 1793888Notes

Reaction equation

HRID 1793888 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH2:15])(=[NH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:16][C:17]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:18]=1[CH:19]=[C:20]([C:23]#[N:24])[C:21]#[N:22]>CO>[NH2:24][C:23]1[C:20]([C:21]#[N:22])=[C:19]([C:18]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:17]=2[Cl:16])[N:15]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 2332BenzamidineHCID 11430Potassium CarbonateHCID 180892,4-Dichlorobenzylidenemalononitrile

Product 1

HCID 155282984-Amino-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (4.34 g, 31.4 mmol) and benzamidine (2.59 g, 21.5 mmol) were added at to a suspension of 2-(2,4-dichloro-benzylidene)-malononitrile (4 g, 17.9 mmol) in methanol. The yellow mixture was stirred for 1 h at room temperature and then heated to reflux for an additional 2 h. After cooling, the solvent was removed at reduced pressure, the residue was taken up in ethyl acetate/ice. The organic phase was separated, washed with water, and dried over sodium sulfate. The solvent was evaporated, the orange residue was taken up in acetone, and 1.91 g potassium manganate was added. After stirring for 90 min, the reaction mixture was filtered through decalite and evaporated. Purification by flash chromatography (silica gel, EtOAc/hexanes) afforded the title compound, MS: m/e=340.8 (M+), as a solid (2.63 g, 43%).

Workup

  1. temperatureheated
  2. temperatureto reflux for an additional 2 h
  3. temperatureAfter cooling
  4. customthe solvent was removed at reduced pressure
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated
  9. addition1.91 g potassium manganate was added
  10. stirringAfter stirring for 90 min
  11. filtrationthe reaction mixture was filtered through decalite
  12. customevaporated
  13. customPurification by flash chromatography (silica gel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-a4cfbfd82255461b8e6fd78f1d0daf9b
Source dataset
uspto-grants-2006_04
Patent number
US07022718B2

Reaction notes

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