Sodium hydride → HCID 57562604, compound

HRID 1725504Notes

Reaction equation

HRID 1725504 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1.[H-].[Na+].[CH3:9][Si:10]([CH3:17])([CH3:16])[CH2:11][CH2:12][O:13][CH2:14]Cl.[Cl-].[NH4+]>CN(C)C=O>[CH3:9][Si:10]([CH3:17])([CH3:16])[CH2:11][CH2:12][O:13][CH2:14][N:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418806HCID 178418806, compound

Product 1

HCID 57562604HCID 57562604, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g of 1H-pyrazol-3-amine in 100 ml of N,N-dimethylformamide was added 9.6 g of sodium hydride (60%, in oil) under cooling with ice. The reaction mixture was stirred for 30 minutes, and then 21.3 ml of 2-(trimethylsilyl)ethoxymethyl chloride was added thereto. After stirring the resulting mixture at room temperature for 1 hour, aqueous ammonium chloride was added thereto, and the mixture was extracted with chloroform. The resulting organic layer was washed with water and brine, and then dried over magnesium sulfate. The organic layer was filtered and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 to 1/2) to give the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring the resulting mixture at room temperature for 1 hour
  3. extractionthe mixture was extracted with chloroform
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 to 1/2)

Sources & evidence

ORD record
ord-565104f6e9054e5c8de6f3f6ccf9f812
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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