Sodium Methoxide → Methyl 3-methoxypyrazine-2-carboxylate

HRID 2264153Notes

Reaction equation

HRID 2264153 reaction equation
Br[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 21418987Methyl 3-methoxypyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2 g of methyl 3-bromopyrazine-2-carboxylate (prepared as described by J. H. Jones, W. H. Holtz, E. J. C. Cragoe, J. Med. Chem., 1969, 12, 285-287) in 50 mL of methanol was added 4 mL of 30% NaOMe in methanol. After stirring 30 min the reaction was quenched with 6 mL of acetic acid and concentrated under reduced pressure. The residue was partitioned between 50 mL ethyl acetate and 50 mL saturated NaHCO3, the extract dried over MgSO4. Concentration under reduced pressure gave a white crystalline solid: MS (m+1)=169.1; 1H NMR (400 MHz, CDCl3) 8.3 (m, 2H), 4.1 (s, 3H), 4.0 (s, 3H).

Workup

  1. customwas quenched with 6 mL of acetic acid
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between 50 mL ethyl acetate and 50 mL saturated NaHCO3
  4. dry with materialthe extract dried over MgSO4
  5. concentrationConcentration under reduced pressure
  6. customgave a white crystalline solid

Sources & evidence

ORD record
ord-f3a82a8a5dec4be69935fba377aaef3b
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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