Methyl iodide → 5-Chloro-1-methylpyrazin-2(1H)-one

HRID 2045993Notes

Reaction equation

HRID 2045993 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:9]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5](=[O:8])[N:6]([CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178516772HCID 178516772, compound

Product 1

HCID 584852805-Chloro-1-methylpyrazin-2(1H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-pyrazin-2-ol (100 mg, 0.76 mmol) in DMF (3 mL) was added K2CO3 (211 mg, 1.53 mmol) and CH3I (0.25 ml, 4 mmol) at room temperature. The mixture was stirred overnight, quenched by H2O, and extracted with EtOAc. The organic phase was concentrated to give the crude product, which was purified by TLC to give 5-chloro-1-methyl-1H-pyrazin-2-one (70 mg, 64%). 1H NMR (CD3OD): δ3.52 (s, 3H), 7.78 (s, 1H), 7.87 (s, 1H).

Workup

  1. customquenched by H2O
  2. extractionextracted with EtOAc
  3. concentrationThe organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by TLC

Sources & evidence

ORD record
ord-6c705502f0c04bddb05a3a25fe0af626
Source dataset
uspto-grants-2013_11
Patent number
US08592410B2

Reaction notes

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