Methyl 6-fluoro-3-nitro-2-pyrazinecarboxylate → Methyl 3-amino-6-fluoropyrazine-2-carboxylate

HRID 392353

Reaction equation

HRID 392353 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-])=O)=[N:4][CH:3]=1.[H][H]>C(O)(=O)C.C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[O-]>[NH2:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([F:1])=[CH:3][N:4]=1

Participants

5

Reactant 2

HCID 22662836Methyl 6-fluoro-3-nitro-2-pyrazinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22662844Methyl 3-amino-6-fluoropyrazine-2-carboxylateYield 11.8%

Reagents, catalysts & solvents 2

HCID 17803853Palladium on calcium carbonateCatalystHCID 176Acetic AcidSolvent

Procedure

In 1.0 mL of acetic acid was dissolved 20 mg of methyl 6-fluoro-3-nitro-2-pyrazinecarboxylate. After adding 6 mg of lead-poisoned palladium-calcium carbonate, hydrogen gas was introduced into the mixture at room temperature under a pressure of 1 atmosphere, until the mixture became absorbing no further quantity of hydrogen gas. The insoluble matter was filtered off from the reaction mixture, and the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 2 mg of methyl 3-amino-6-fluoro-2-pyrazinecarboxylate as a light yellow-colored solid product.

Workup

  1. additionwas introduced into the mixture at room temperature under a pressure of 1 atmosphere, until the mixture
  2. custombecame absorbing no further quantity of hydrogen gas
  3. filtrationThe insoluble matter was filtered off from the reaction mixture
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-27d2ce7a66aa4c38ae6390899a0cf153
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Linked notes

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