Phosphorus oxybromide → Methyl 5-bromopyrazine-2-carboxylate

HRID 1421727Notes

Reaction equation

HRID 1421727 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](O)=[CH:7][N:6]=1)=[O:4].P(Br)(Br)([Br:14])=O>CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([Br:14])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178498852HCID 178498852, compound

Product 1

HCID 27282430Methyl 5-bromopyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-hydroxy-pyrazine-2-carboxylic acid methyl ester (2.56 g, 16.61 mmol) in phosphorous oxybromide 9.9 g, 34.9 mmol) were heated at 90° C. for 70 mins. The reaction was allowed to cool and the resulting solid carefully dissolved in methanol and then the solvent was evaporated in vacuo. The residue was partitioned between EtOAc and sat. NaHCO3 and the organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc:Hexanes 40:60) to afford the title compound.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was partitioned between EtOAc and sat. NaHCO3
  4. washthe organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed (silica gel, EtOAc:Hexanes 40:60)

Sources & evidence

ORD record
ord-cce7aef667164276a12bc3a4865c0a95
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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