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

HRID 983834

반응식

HRID 983834 반응식
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

참가 물질

5

반응물 3

HCID 2332BenzamidineHCID 11430Potassium CarbonateHCID 180892,4-Dichlorobenzylidenemalononitrile

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0b178cea07b843ff802bcb4843afdceb
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867205B2

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