Water → HCID 178513810, compound

HRID 392306Notes

Reaction equation

HRID 392306 reaction equation
[I-].[Na+].C[Si](Cl)(C)C.[F:8][C:9]1[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[C:12]([O:18]C)=[N:11][CH:10]=1.O>C(#N)C.C(Cl)(Cl)Cl>[F:8][C:9]1[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[C:12]([OH:18])=[N:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 22662826HCID 22662826, compound

Product 1

HCID 178513810HCID 178513810, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

In an atmosphere of nitrogen gas, 1.51 g of sodium iodide was dissolved in 22 mL of acetonitrile. After adding 1.10 g of trimethylsilyl chloride, the mixture thus obtained was stirred at room temperature for 20 minutes. Then, 0.43 g of 6-fluoro-3-methoxy-2-pyrazinecarboxamide was added, and the mixture thus obtained was stirred at the same temperature as above for 18 hours. The reaction mixture was added to a mixture of 10 mL of water and 200 mL of chloroform, and the mixture thus formed was separated into layers. The organic layer was washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography [eluent: hexane:ethyl acetate=2:1] to obtain 0.06 g of 6-fluoro-3-hydroxy-2-pyrazinecarboxamide as a white-colored solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringwas stirred at the same temperature as above for 18 hours
  4. customthe mixture thus formed
  5. customwas separated into layers
  6. washThe organic layer was washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  7. dry with materialdried on anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by column chromatography [eluent: hexane:ethyl acetate=2:1]

Sources & evidence

ORD record
ord-1341f1bdd1b34ab4b49e7ec145751c5b
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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