Water → 1243817-09-5

HRID 1842858Notes

Reaction equation

HRID 1842858 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]#[N:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([CH3:14])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178441039HCID 178441039, compound

Product 1

HCID 666440481243817-09-5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-tert.-butyl-1H-pyrazol-5-carbonitrile (J-IV) (10 mmol) was added to a suspension of NaH (60%) (12.5 mmol) in DMF (20 ml) at room temperature while stirring. After stirring for 15 minutes, methyl iodide (37.5 mmol) was added dropwise to this reaction mixture at room temperature. After stirring for 30 min at 100° C., the reaction mixture was mixed with water (150 ml) and extracted with dichloromethane (3×75 ml). The combined organic extracts were washed with water (100 ml) and sat. NaCl solution (100 ml) and dried over magnesium sulfate. After removal of the solvent under vacuum, the residue was purified by column chromatography (SiO2, various mixtures of EtOAc and cyclohexane as the mobile solvent) and the product J-V was obtained.

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringAfter stirring for 30 min at 100° C.
  3. extractionextracted with dichloromethane (3×75 ml)
  4. washThe combined organic extracts were washed with water (100 ml) and sat. NaCl solution (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent under vacuum
  7. customthe residue was purified by column chromatography (SiO2, various mixtures of EtOAc and cyclohexane as the mobile solvent) and the product J-V
  8. customwas obtained

Sources & evidence

ORD record
ord-3e4431a63390417d8818428665f2462f
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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