2-Pyrazinecarbonitrile, 3-azido-6-fluoro- → HCID 22662784, compound

HRID 392347

Reaction equation

HRID 392347 reaction equation
[N:1]([C:4]1[C:5]([C:11]#[N:12])=[N:6][C:7]([F:10])=[CH:8][N:9]=1)=[N+]=[N-].[H][H]>CO.C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[O-]>[NH2:1][C:4]1[C:5]([C:11]#[N:12])=[N:6][C:7]([F:10])=[CH:8][N:9]=1

Participants

5

Reactant 2

HCID 226627892-Pyrazinecarbonitrile, 3-azido-6-fluoro-HCID 178418361HCID 178418361, compound2×

Product 1

HCID 22662784HCID 22662784, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 17803853Palladium on calcium carbonateCatalystHCID 887MethanolSolvent

Procedure

In 5.0 mL of methanol was dissolved 0.24 g of 3-azido-6-fluoro-2-pyrazinecarbonitrile. After adding 0.075 g of lead-poisoned palladium-calcium carbonate at room temperature, hydrogen gas was introduced into the mixture at room temperature under a pressure of 1 atmosphere until the mixture became showing no further adsorption of hydrogen. After filtering off the insoluble matter from the reaction mixture, the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: chloroform] to obtain 0.078 g of 3-amino-6-fluoro-2-pyrazinecarbonitrile as a yellow-colored solid product.

Workup

  1. filtrationAfter filtering off the insoluble matter from the reaction mixture
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel column chromatography [eluent: chloroform]

Sources & evidence

ORD record
ord-4480d28c37a24f63a3f2cd8e179bbf7d
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Linked notes

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