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

HRID 2359034Notes

Reaction equation

HRID 2359034 reaction equation
[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

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 178503424HCID 178503424, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7600c8c8aee840b5ba9d0f3cc75140a0
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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