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

HRID 2192917Notes

Reaction equation

HRID 2192917 reaction equation
[OH:1][CH:2]([C:4]1[N:5]=[CH:6][C:7]([NH:10]C(=O)C(C)(C)C)=[N:8][CH:9]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[Na+].O>[NH2:10][C:7]1[N:8]=[CH:9][C:4]([CH:2]([OH:1])[CH3:3])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium Carbonate2×HCID 59571026N-[5-(1-hydroxyethyl)pyrazin-2-yl]-2,2-dimethylpropanamide

Product 1

HCID 552840111-(5-Aminopyrazin-2-yl)ethanolYield 76.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-[5-(1-hydroxyethyl)pyrazin-2-yl]-2,2-dimethylpropanamide (394 mg) in methanol (10 mL) was added potassium carbonate (249 mg) at room temperature, followed by stirring at room temperature overnight and stirring at 60° C. for 5 hours. Further, potassium carbonate (249 mg) was added thereto, followed by stirring at 60° C. for 3 hours. After leaving it to be cooled to room temperature, saturated brine was added to the reaction mixture, 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)ethanol (187 mg) as a pale yellow solid.

Workup

  1. stirringstirring at 60° C. for 5 hours
  2. stirringby stirring at 60° C. for 3 hours
  3. customAfter leaving it
  4. temperatureto be cooled to room temperature
  5. extractionfollowed by extraction with a solvent (chloroform:isopropyl alcohol=4:1)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. filtrationThe obtained solid was collected by filtration
  9. washwhile washing with a solvent (hexane:diisopropyl ether=1:1)

Sources & evidence

ORD record
ord-e78e588916db456aa5a5293e6830f8e6
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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