Methanol → 5-Chloro-2-methoxypyrido[3,4-b]pyrazine

HRID 627612Notes

Reaction equation

HRID 627612 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[C:5]2=[N:6][CH:7]=1.[CH3:13][O-:14].[Na+].CO>CN(C)C=O.O>[Cl:12][C:8]1[C:5]2=[N:6][CH:7]=[C:2]([O:14][CH3:13])[N:3]=[C:4]2[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 867157432,5-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 867157445-Chloro-2-methoxypyrido[3,4-b]pyrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dichloropyrido[3,4-b]pyrazine (580 mg, 2.90 mmol) in N,N-dimethylformamide (10 mL) was added a 0.5-M solution of sodium methoxide in methanol (6.09 mL, 3.04 mmol), and the reaction was stirred at room temperature for 5 minutes. The solution was diluted with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate, filtered and concentrated to afford the title compound (550 mg, 2.81 mmol). MS m/z=196 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21cc8c295a194b5783a4c40b360093fe
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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