Sodium Methoxide → 3-Chloro-5-methoxypyrazine-2-carbaldehyde

HRID 1609847Notes

Reaction equation

HRID 1609847 reaction equation
[Cl:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.[CH3:11][O-:12].[Na+]>CO>[Cl:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[C:6]([O:12][CH3:11])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 156968403,5-Dichloropyrazine-2-carbaldehyde

Product 1

HCID 222603943-Chloro-5-methoxypyrazine-2-carbaldehydeYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-dichloro-pyrazine-2-carbaldehyde (150 mg, 0.85 mmol) in methanol (5 mL) is added sodium methoxide (25% w/w in MeOH, 183 mg, 0.85 mmol) at 0° C. After the mixture is stirred at 0° C. for 2 hours and then at room temperature overnight, the reaction is quenched with saturated NH4Cl (1 mL) and solvent removed in vacuo until dryness. DCM (20 mL) is added, and the solution is dried and solvent removed to give 140 mg of 3-chloro-5-methoxy-pyrazine-2-carbaldehyde as an oil.

Workup

  1. customat room temperature overnight, the reaction is quenched with saturated NH4Cl (1 mL) and solvent
  2. customremoved in vacuo until dryness
  3. additionDCM (20 mL) is added
  4. customthe solution is dried
  5. customsolvent removed

Sources & evidence

ORD record
ord-d96d935bf3e0465394792c35ecffd597
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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