Sodium Methoxide → 3-(Methyloxy)-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine

HRID 657075Notes

Reaction equation

HRID 657075 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.[CH3:22][O-:23].[Na+]>CO>[CH3:22][O:23][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 594373343-Bromo-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine

Product 1

HCID 594373643-(Methyloxy)-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Bromo-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine (1.19 g, 3.44 mmol) was suspended in methanol and a solution of sodium methoxide (25% in methanol, 10.1 mL) was added at room temperature under argon. After 20 min all the solid went into solution, the reaction was stirred overnight at rt. The solvent was removed and the residue partitioned between water (250 mL) and 10% MeOH/DCM (200 mL). The aqueous phase was extracted with 10% MeOH/DCM (2×100 mL). The combined organic phases were dried, evaporated and subjected to column chromatography on silica gel eluting with DCM to afford 0.6 g of the title compound (59%).

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between water (250 mL) and 10% MeOH/DCM (200 mL)
  3. extractionThe aqueous phase was extracted with 10% MeOH/DCM (2×100 mL)
  4. customThe combined organic phases were dried
  5. customevaporated

Sources & evidence

ORD record
ord-bee7e6d41f324e8a9e0d28408f90397c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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