Isopropyl iodide → 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine

HRID 2359034ノート

反応式

HRID 2359034 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[CH:10][NH:9][N:8]=2)=[CH:4][CH:3]=1.I[CH:21]([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[CH:10][N:9]([CH:21]([CH3:23])[CH3:22])[N:8]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 178503424HCID 178503424、化合物

生成物 1

HCID 672607724-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine収率 73.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidin (1 eq, 16.2 mmol) in 120 mL N,N-dimethylformamide were added 2-iodopropane (1.5 eq, 24.3 mmol) and cesium carbonate (1.1 eq, 17.8 mmol). The reaction mixture was stirred at room temperature for 4 h and the solvent was then evaporated. The residue was diluted with water and dichloromethane. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane) to afford 4.2 g of 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidin (70% yield).

後処理

  1. customthe solvent was then evaporated
  2. additionThe residue was diluted with water and dichloromethane
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted three times with dichloromethane
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (dichloromethane)

出典と根拠

ORDレコード
ord-7600c8c8aee840b5ba9d0f3cc75140a0
出典データセット
uspto-grants-2014_04
特許番号
US08685974B2

反応ノート

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