2-Pyrazinecarboxylic acid → Methyl pyrazinoate

HRID 2243885Notes

Reaction equation

HRID 2243885 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:10][O:8][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

5

Reactant 3

HCID 10472-Pyrazinecarboxylic acidHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 72662Methyl pyrazinoateYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To pyrazine-2-carboxylic acid (15.0 g, 121 mmol) in DMF (150 mL) were added K2CO3 (50 g, 363 mmol) and MeI (9.0 mL, 145 mmol). After stirring for 3 days, the reaction mixture was filtered and then concentrated. The residue was dissolved in ethyl acetate, washed with water (3 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by flash column chromatography eluted with 10-30% ethyl acetate in hexanes gave the title product (1.28 g, 8%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water (3 times) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography
  9. washeluted with 10-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-54b0abc5b09f44d5a3c906f19fcb7c5f
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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