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

HRID 930445Notes

Reaction equation

HRID 930445 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 RT 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-25e5e84694274dc9b3852a6834410aa4
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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