Sodium Hydroxide → HCID 135815258, compound

HRID 1977628Notes

Reaction equation

HRID 1977628 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=O)[CH3:21])=[CH:15][CH:14]=3)=[N:6][C:5]=2[C:4]([CH2:23][CH2:24][CH3:25])=[N:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:7]2[NH:8][C:9](=[O:11])[C:10]3[N:2]([CH3:1])[N:3]=[C:4]([CH2:23][CH2:24][CH3:25])[C:5]=3[N:6]=2)=[CH:14][CH:15]=1)[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 135815269HCID 135815269, compound

Product 1

HCID 135815258HCID 135815258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{4-[(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)methyl]phenyl}acetamide (2.37 g, 0.007 mol) was added to a mixture of lithium aluminium hydride (705 mg, 0.0186 mol) in tetrahydrofuran (250 ml), under a nitrogen atmosphere. After the effervescence had subsided, the reaction was refluxed for 2 hours. On cooling, the mixture was treated dropwise with aqueous sodium hydroxide solution (5M, 1.1 ml), and the resulting solid filtered and washed well with tetrahydrofuran (250 ml). The filtrate was concentrated under reduced pressure and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous phase was extracted with ethyl acetate (200 ml) and the organic phases combined, dried (MgSO4), filtered and concentrated under reduced pressure.

Workup

  1. temperaturethe reaction was refluxed for 2 hours
  2. temperatureOn cooling
  3. filtrationthe resulting solid filtered
  4. washwashed well with tetrahydrofuran (250 ml)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  7. extractionThe aqueous phase was extracted with ethyl acetate (200 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ea5614562f4406a8833b8e2aa25a31e
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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