Water → HCID 178513810, compound

HRID 1005743Notes

Reaction equation

HRID 1005743 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 a nitrogen atmosphere, 1.51 g of sodium iodide is dissolved in 22 mL of acetonitrile. Then, 1.10 g of trimethylsilyl chloride is added thereto. The resulting solution is stirred at ambient temperature for 20 minutes. Then, 0.43 g of 6-fluoro-3-methoxy-2-pyrazinecarboxamide is added thereto. The resulting solution is stirred at the same temperature as above for 18 hours. Then, a mixture of 10 mL of water and 200 mL of chloroform is added to the reaction mixture, and separated into layers. The organic layer thus obtained is washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure. The residue thus obtained is purified by column chromatography (eluent: hexane:ethyl acetate=2:1) to obtain 0.06 g of 6-fluoro-3-hydroxy-2-pyrazinecarboxamide.

Workup

  1. stirringThe resulting solution is stirred at the same temperature as above for 18 hours
  2. additionis added to the reaction mixture
  3. customseparated into layers
  4. customThe organic layer thus obtained
  5. washis washed successively with 5% aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by column chromatography (eluent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a0d3471ced27423c896556db0b57baf5
Source dataset
uspto-grants-2004_09
Patent number
US06787544B2

Reaction notes

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