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

HRID 1454798Notes

Reaction equation

HRID 1454798 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 (50% then 100% ethyl acetate/hexane) afforded the title compound as a yellow solid. 1H-NMR (500 MHz, CDCl3): δ 8.42 (d, 1H, J=4.6 Hz), 8.67 (dd, 1H, J=1.4 and 4.6 Hz), 9.47 (d, 1H, J=1.4 Hz). LC/MS 189 (M+1).

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

Sources & evidence

ORD record
ord-13c09cadc3e24acba63dc696f53e0aea
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

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