Methyl iodide → Methyl 3-chloropyrazine-2-carboxylate

HRID 473748Notes

Reaction equation

HRID 473748 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 15019003-Chloro-2-pyrazine-carboxylic acid

Product 1

HCID 1519497Methyl 3-chloropyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-chloropyrazine-2-carboxylic acid (10 g, 63 mmol) and cesium carbonate (31 g, 95 mmol) in DMF was added iodomethane (5.9 ml, 95 mmol). The solution was stirred for 48 hours. After that time, the reaction was removed from stirring, acidified to pH 5 with 1.0 N HCl and extracted five times with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated, affording to target material as an orange oil. MS (ESI, pos. ion) m/z: 173.0 (M+1).

Workup

  1. customAfter that time, the reaction was removed
  2. stirringfrom stirring
  3. extractionextracted five times with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customaffording

Sources & evidence

ORD record
ord-a9da39d2f2a24814951eb10364b1bdd1
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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