Water → HCID 178513802, compound

HRID 1005748Notes

Reaction equation

HRID 1005748 reaction equation
[F:1][C:2]1[N:3]=[C:4]([O:11]C)[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C.C(Cl)(Cl)Cl>[F:1][C:2]1[N:3]=[C:4]([OH:11])[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 22674952HCID 22674952, compound

Product 1

HCID 178513802HCID 178513802, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

In a nitrogen atmosphere, 0.09 g of 5-fluoro-3-methoxy-2-pyrazinecarboxamide is suspended in 3.6 mL of acetonitrile. Then, 0.16 g of sodium iodide and 0.11 g of chlorotrimethylsilane are successively added to the suspension, which is then stirred at ambient temperature for 20 hours. Then, 2 mL of water and 40 mL of chloroform are added to the reaction mixture and separated into layers. The organic layer is separated, washed successively with 5% (w/v) aqueous solution of magnesium thiosulfate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Then, the solvent is distilled off under reduced pressure. The residue thus obtained is purified by column chromatography (eluent: chloroform) to obtain 0.01 g of 5-fluoro-3-hydroxy-2-pyrazinecarboxamide.

Workup

  1. customseparated into layers
  2. customThe organic layer is separated
  3. washwashed successively with 5% (w/v) aqueous solution of magnesium thiosulfate and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-540d6619b7ad492a8edbe0292f1fb97d
Source dataset
uspto-grants-2004_09
Patent number
US06787544B2

Reaction notes

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