Dimethylformamide → HCID 66872342, compound

HRID 1931310Notes

Reaction equation

HRID 1931310 reaction equation
[H-].[Na+].CN(C=O)C.[CH:8]([O:11][C:12]1[NH:16][N:15]=[C:14]([NH2:17])[CH:13]=1)([CH3:10])[CH3:9].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>C(OCC)(=O)C>[CH:8]([O:11][C:12]1[N:16]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[N:15]=[C:14]([NH2:17])[CH:13]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 1784587215-Isopropoxy-1H-pyrazol-3-amine

Product 1

HCID 66872342HCID 66872342, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60%, 425 mg, 10.63 mmol) was added to a DMF (mL) solution of 5-isopropoxy-1H-pyrazole-3-amine (1.5 g, 10.63 mmol) at −18 degrees, and the mixture was stirred for 30 minutes. Then, 2-(trimethylsilyl)ethoxymethyl chloride (1.89 mL, 10.63 mmol) was added dropwise, and stirred at room temperature for 24 hours. The reaction mixture was then diluted with ethyl acetate, and washed once with distilled water, and once with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the title compound (462 mg, 16%).

Workup

  1. stirringstirred at room temperature for 24 hours
  2. washwashed once with distilled water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was then purified

Sources & evidence

ORD record
ord-ba4289d1839c40309caf5ed1b0a2c5f5
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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