Dimethylformamide → 4-(4-Methylphenyl)-5-pyrimidinecarbonitrile

HRID 274584ノート

反応式

HRID 274584 の反応式
Br[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:15][N:16](C=O)C>Cl.O.C(OCC)(=O)C>[C:15]([C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:4][CH:5]=[N:6][CH:7]=1)#[N:16]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 200930065-Bromo-4-(4-methylphenyl)pyrimidine

生成物 1

HCID 200929434-(4-Methylphenyl)-5-pyrimidinecarbonitrile

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5-bromo-4-(p-tolyl)pyrimidine (10 g, 40.2 mmol) and cuprous cyanide (4.4 g, 44.2 mmol) in DMF (20 ml) was heated under reflux for 3 hours. To the reaction mixture was added a solution of ferric chloride. 6 hydrate (13 g, 48.2 mmol) in a mixture of hydrochloric acid (7 ml) and water (55 ml) and the mixture was heated at 50° C. for 10 minutes. After the reaction solution was taken up in ethyl acetate and water, the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated to dryness. The residue was purified by column chromatography on silica gel to give a crystalline product. Recrystallization from isopropyl ether-hexane afforded colorless needles (5 g, 64%), m.p. 127°-128° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionwater, the mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel
  7. customto give a crystalline product
  8. customRecrystallization from isopropyl ether-hexane afforded colorless needles (5 g, 64%), m.p. 127°-128° C.

出典と根拠

ORDレコード
ord-b41b331aee6540268c6389b14700d708
出典データセット
uspto-grants-1995_02
特許番号
US05389641

反応ノート

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