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

HRID 983834

反応式

HRID 983834 の反応式
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

参加物

5

反応物 3

HCID 2332BenzamidineHCID 11430Potassium CarbonateHCID 180892,4-Dichlorobenzylidenemalononitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-0b178cea07b843ff802bcb4843afdceb
出典データセット
uspto-grants-2005_03
特許番号
US06867205B2

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