Chloroform → HCID 22674952, compound

HRID 1005735Notes

Reaction equation

HRID 1005735 reaction equation
N[C:2]1[N:3]=[C:4]([O:11][CH3:12])[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.N([O-])=O.[Na+].C(Cl)(Cl)Cl.[FH:21].N1C=CC=CC=1>>[F:21][C:2]1[N:3]=[C:4]([O:11][CH3:12])[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 64774Pyridine, hydrofluoride (1:1)HCID 22674954HCID 22674954, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22674952HCID 22674952, compound

Conditions

Temperature
-10 °C

Procedure

In a nitrogen atmosphere, 0.5 g of 5-amino-3-methoxy-2-pyrazinecarboxamide is dissolved in 9 mL of 70% pyridine hydrofluoride under ice-cooling. Then, 0.23 g of sodium nitrite is added thereto at −70° C., and the resulting solution is heated to a temperature of −10° C. in 30 minutes. Further, the solution is stirred at ambient temperature for 30 minutes. A mixture of 30 mL of ice water and 100 mL of chloroform is added thereto and the resulting mixture is separated into layers. The organic layer is washed with 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: chloroform:methanol =10:1) to obtain 0.37 q of 5-fluoro-3-methoxy-2-pyrazinecarboxamide.

Workup

  1. temperaturecooling
  2. additionis added
  3. customthe resulting mixture is separated into layers
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by column chromatography (eluent: chloroform:methanol =10:1)

Sources & evidence

ORD record
ord-a07567524f1a4c5982aed75ca563e932
Source dataset
uspto-grants-2004_09
Patent number
US06787544B2

Reaction notes

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