Hydrochloric Acid → N-[5-(1-hydroxyethyl)pyrazin-2-yl]-2,2-dimethylpropanamide

HRID 2192916Notes

Reaction equation

HRID 2192916 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+].Cl>C(O)C.C1COCC1>[OH:3][CH:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21897264N-(5-acetylpyrazin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 59571026N-[5-(1-hydroxyethyl)pyrazin-2-yl]-2,2-dimethylpropanamideYield 104.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-acetylpyrazin-2-yl)-2,2-dimethylpropanamide (500 mg) in ethanol (10 mL) and THF (10 mL) was added sodium borohydride (86 mg) under ice-cooling, followed by stirring for 30 minutes under ice-cooling. To the reaction mixture was added 1 M hydrochloric acid under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated to obtain N-[5-(1-hydroxyethyl)pyrazin-2-yl]-2,2-dimethylpropanamide (525 mg) as a brown solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb521ee5fdc84de1b8e868c88484cbd3
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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