Ammonium Hydroxide → 2-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine

HRID 241554Notes

Reaction equation

HRID 241554 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3](=[N:11]O)[NH:4][C:5]1[CH:10]=[N:9][CH:8]=[CH:7][N:6]=1.[OH-].[NH4+]>>[F:1][C:2]([F:14])([F:13])[C:3]1[N:4]=[C:5]2[CH:10]=[N:9][CH:8]=[CH:7][N:6]2[N:11]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 178526369HCID 178526369, compound

Product 1

HCID 533933572-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine

Conditions

Temperature
150 °C

Procedure

A mixture of 2,2,2-trifluoro-N′-hydroxy-N-pyrazin-2-ylethanimidamide (10.5 g, 50.97 mmol, from Step B) and polyphosphoric acid (80 mL) was heated to 150° C. with stirring for 18 h. The solution was added to ice and neutralized by addition of ammonium hydroxide. The dark aqueous solution was extracted three times with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography (eluting with 50% followed by 100% ethyl acetate/hexane) afforded the title compound as a yellow solid.

Workup

  1. additionThe solution was added to ice
  2. extractionThe dark aqueous solution was extracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration
  6. washfollowed by flash chromatography (eluting with 50% followed by 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-96665976fa574224acff39219859ad5d
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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