Pyrazole → 2-(1H-Pyrazol-1-yl)pyrimidine

HRID 1038120ノート

反応式

HRID 1038120 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(OCC)(=O)C>CC(N(C)C)=O.[Cu]I.O>[N:1]1([C:7]2[N:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

参加物

8

反応物 4

HCID 1048PyrazoleHCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 783452-Bromopyrimidine

生成物 1

HCID 111707712-(1H-Pyrazol-1-yl)pyrimidine収率 15.7%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

A reaction mixture containing pyrazole (2 g, 29 mmol), 2-bromopyrimidine (3.8 g, 24 mmol), copper (I) iodide (0.91 g, 4.8 mmol) and 1,10-phenanthroline (1.7 g, 9.6 mmol) in DMA was heated at 140° C. in a sealed tube for 6 hours. After the reaction, ethyl acetate (30 mL) was added, followed by water. The aqueous layer was extract three times (20 mL) and the organic layer was collected, dry over sodium sulfate. After concentration under vacuum, the crude product was purified using column chromatography (10% ethyl acetate in dichloromethane) to give 0.55 g of pure product. 15% yield. MS (ESMS, M+H 146).

後処理

  1. additionwas added
  2. extractionThe aqueous layer was extract three times (20 mL)
  3. customthe organic layer was collected
  4. dry with materialdry over sodium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe crude product was purified

出典と根拠

ORDレコード
ord-def692fd8412499c9e784ff4a9993002
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

反応ノート

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