Potassium Carbonate → 1-(5-Aminopyrazin-2-yl)ethanone

HRID 2192918Notes

Reaction equation

HRID 2192918 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10]C(=O)C(C)(C)C)=[N:8][CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[NH2:10][C:7]1[N:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 21897264N-(5-acetylpyrazin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 180049531-(5-Aminopyrazin-2-yl)ethanoneYield 96.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(5-acetylpyrazin-2-yl)-2,2-dimethylpropanamide (300 mg) in methanol (10 mL) was added potassium carbonate (750 mg) at room temperature. It was stirred at 60° C. overnight. To the reaction mixture were added saturated aqueous sodium bicarbonate and saturated brine at room temperature, followed by extraction with a solvent (chloroform:isopropyl alcohol=4:1). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained solid was collected by filtration while washing with a solvent (hexane:diisopropyl ether=1:1), to obtain 1-(5-aminopyrazin-2-yl)ethanone (180 mg) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with a solvent (chloroform:isopropyl alcohol=4:1)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. filtrationThe obtained solid was collected by filtration
  5. washwhile washing with a solvent (hexane:diisopropyl ether=1:1)

Sources & evidence

ORD record
ord-8f7ee95e8e4d4b57bee521ac28571284
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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