Water → HCID 22249949, compound

HRID 584828Notes

Reaction equation

HRID 584828 reaction equation
[H-].[Na+].[CH2:3]([CH:5]([N:8]1[C:16](=[O:17])[NH:15][C:14]2[C:13]([CH3:18])=[N:12][C:11]3=[C:19]([C:23]4[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[CH3:31])[C:20]([CH3:22])=[N:21][N:10]3[C:9]1=2)[CH2:6][CH3:7])[CH3:4].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[CH2:32]([N:15]1[C:14]2[C:13]([CH3:18])=[N:12][C:11]3=[C:19]([C:23]4[C:24]([CH3:31])=[CH:25][C:26]([CH3:30])=[CH:27][C:28]=4[CH3:29])[C:20]([CH3:22])=[N:21][N:10]3[C:9]=2[N:8]([CH:5]([CH2:6][CH3:7])[CH2:3][CH3:4])[C:16]1=[O:17])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22249617HCID 22249617, compound

Product 1

HCID 22249949HCID 22249949, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (28 mg, 0.71 mmol) was added to a solution of 1-(1-ethylpropyl)-6-mesityl-4,7-dimethyl-2,3-dihydro-1H-pyrazolo[5,1-b]purin-2-one (230 mg, 0.59 mmol) in N,N-dimethylformamide (5 mL) at room temperature. After 30 minutes, benzyl bromide (0.079 mL, 0.65 mmol) was added, followed by stirring at 70′ for one hour. Water was added under ice-cooling, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (15-20% ethylacetate/hexane), to give the title compound (259 mg) as brown crystals.

Workup

  1. temperaturecooling
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (15-20% ethylacetate/hexane)

Sources & evidence

ORD record
ord-8e99e25b9cca4db2b94c54b5f27f9aae
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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