1H-1,2,4-Triazole → 2-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrazine

HRID 2067185Notes

Reaction equation

HRID 2067185 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11](Cl)[N:10]=1>CN(C=O)C.CCOC(C)=O.O>[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[N:10]=1

Participants

7

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 432604282-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,2,4-triazole (276 mg, 4.0 mmol, 2.0 eq) in 1.5 mL of DMF was added carefully sodium hydride (60 wt. %. in mineral oil, 120 mg, 3.0 mmol, 3.0 eq) (caution: intensive gas development). The reaction mixture was stirred at room temperature for 45 min. 2,6-Dichloropyrazine (298 mg, 2.0 mmol, 1.0 eq) in 0.5 mL of DMF was added and the reaction mixture was heated at 95° C. for 60 min. The mixture was allowed to cool to room temperature and diluted with EtOAc (15 mL) and water (15 mL). The separated organic layer was concentrated under reduced pressure to afford crude material containing the title compound. The crude material was suspended in NMP (2 mL) and directly used in coupling reactions with phenols. ES/MS m/z 182.0, (MH+), Rt=1.68 min.

Workup

  1. temperaturethe reaction mixture was heated at 95° C. for 60 min
  2. temperatureto cool to room temperature
  3. concentrationThe separated organic layer was concentrated under reduced pressure
  4. customto afford crude material

Sources & evidence

ORD record
ord-a973dccbbbd54e79b1737eb017c11f36
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

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