Ammonium formate → HCID 54384494, compound

HRID 1444070Notes

Reaction equation

HRID 1444070 reaction equation
Br[C:2]1[N:3]=[C:4]([O:10][CH3:11])[C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:11][O:10][C:4]1[C:5]([NH2:9])=[N:6][C:7]([CH3:8])=[CH:2][N:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59168136HCID 59168136, compound

Product 1

HCID 54384494HCID 54384494, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-3-methoxy-6-methyl-2-pyrazinamine (Example 118c) (0.8 g) and ammonium formate (0.4 g) in methanol (20 mL) was added palladium on carbon (0.2 g) and the reaction mixture heated at reflux for 5h. After cooling to room temperature, the reaction mixture was filtered through a plug of celite, and the filtrate evaporated. The residue was partitioned between dichloromethane and water, and the organic phase dried (MgSO4), filtered and evaporated to give the title compound as a white solid (0.44 g).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 5h
  3. filtrationthe reaction mixture was filtered through a plug of celite
  4. customthe filtrate evaporated
  5. customThe residue was partitioned between dichloromethane and water
  6. dry with materialthe organic phase dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2c4ae69f60534046b6a81935b3227723
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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