Ammonium Hydroxide → 3-(Trifluoromethyl)-1,2,4-triazolo(4,3-a)pyrazine
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][NH:6][C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)=O.[NH4+].[OH-]>O>[F:1][C:2]([F:14])([F:13])[C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]2=[N:6][N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To title compound 477 (3.12 g, 15.14 mmol) was added PPA (15 mL). The mixture was heated to 150° C. for 1 h then poured over water. The aqueous was basified with conc. NH4OH (exotherm) at 0° C. Water was added until everything was dissolved. The mixture was extracted with ethyl acetate (×4). The organics were washed with brine, died over Na2SO4, filtered and concentrated to a brown paste. The residue was purified by flash chromatography (0% to 70% ethyl acetate in hexanes) to afford title compound 478 (0.9 g, 32%) as a brown solid. MS (m/z): 189.1 (M+H).
Workup
- dissolutionwas dissolved
- extractionThe mixture was extracted with ethyl acetate (×4)
- washThe organics were washed with brine
- filtrationfiltered
- concentrationconcentrated to a brown paste
- customThe residue was purified by flash chromatography (0% to 70% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-8a7153c7457a4ae1be5c63b75d1fefce
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193749B2
Reaction notes
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