Water → 2-chloro-5-(1H-1,2,4-triazol-1-yl)pyrazine

HRID 1039066Notes

Reaction equation

HRID 1039066 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[CH:4][N:3]=1.[NH:9]1[CH:13]=[N:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 3362242,5-Dichloropyrazine

Product 1

HCID 772311952-chloro-5-(1H-1,2,4-triazol-1-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichloropyrazine (298 mg, 2.0 mmol) and 1,2,4-triazole (145 mg, 2.1 mmol) were added in DMF (10 mL), then cesium carbonate was added and the reaction was at room temperature over night. Water (20mL) was added, extracted with ethyl acetate (30 mL), second wash with brine (20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 22% ethyl acetate/hexanes to give the title compound as a white solid.

Workup

  1. waitthe reaction was at room temperature over night
  2. extractionextracted with ethyl acetate (30 mL)
  3. washsecond wash with brine (20 mL)
  4. dry with materialThe organic phase was dried by magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge
  8. washeluting with 22% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6aa25653d514468d93269044bf045558
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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