Sodium hydride → 1-[3-(benzyloxy)propyl]-1H-pyrazol-3-amine

HRID 2192885Notes

Reaction equation

HRID 2192885 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([NH2:8])=[N:4]1.Br[CH2:10][CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:14]([O:13][CH2:12][CH2:11][CH2:10][N:3]1[CH:7]=[CH:6][C:5]([NH2:8])=[N:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 178418806HCID 178418806, compound

Product 1

HCID 595709031-[3-(benzyloxy)propyl]-1H-pyrazol-3-amineYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 60% sodium hydride (496 mg) in DMF (10 mL) was added a solution of 1H-pyrazol-3-amine (1.03 g) in DMF (5 mL) under ice-cooling, followed by stirring at room temperature for 30 minutes. A solution of [(3-bromopropoxy)methyl]benzene (2.93 g) in DMF (10 mL) was added thereto under ice-cooling, followed by stirring at room temperature overnight. Saturated brine and saturated aqueous sodium bicarbonate were added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:1-1:3) to obtain 1-[3-(benzyloxy)propyl]-1H-pyrazol-3-amine (835 mg) as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature overnight
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1-1:3)

Sources & evidence

ORD record
ord-33af06a8852d42d291d6ab26f4d4c07b
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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