Sodium Methoxide → 5-Amino-3-methoxypyrazine-2-carbonitrile

HRID 40659

Reaction equation

HRID 40659 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[N:6]=[C:7](Cl)[C:8]([C:11]#[N:12])=[N:9][CH:10]=1>O1CCOCC1>[NH2:4][C:5]1[N:6]=[C:7]([O:2][CH3:1])[C:8]([C:11]#[N:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 210753925-Amino-3-chloropyrazine-2-carbonitrile

Product 1

HCID 596133845-Amino-3-methoxypyrazine-2-carbonitrileYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Sodium methoxide (70 mg, 1.29 mmol) was added to a stirred solution of 5-amino-3-chloropyrazine-2-carbonitrile (100 mg, 0.647 mmol) in dioxane (1 mL). The reaction mixture was heated in a sealed tube at 90° C. overnight. The solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give the title compound (32 mg, 0.213 mmol, 33%). LC-MS (3) Rt=0.96 min; m/z (ESI+) 151 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was re-extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2a58f12c95ea497d9bd50b79913e99b6
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Linked notes

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