Hydrochloric Acid → 7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:18])=O.Cl>>[Cl:18][C:6]1[N:5]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1Participants
Procedure
A mixture of 0.750 g (3.44 mmol) 5-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol and 1.35 mL (14.46 mmol) of phosphorus oxychloride was heated under reflux for 60 minutes, during which time the pinkish solid dissolved gradually with the evolution of hydrogen chloride gas. The resultant dark red solution was distilled under reduced pressure to remove excess phosphorus oxychloride and the residue triturated with ice-water. The resultant aqueous solution was extracted with methylene chloride, the organic layer thus obtained was dried and the solvent was removed to give the desired product. Further washes of the crude residue with methylene chloride gave 0.547 g of 7-chloro-5-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine. Yield 67.4%. The washed crude was used without purification in the next step.
Workup
- temperaturewas heated
- temperatureunder reflux for 60 minutes, during which time the pinkish solid
- distillationThe resultant dark red solution was distilled under reduced pressure
- customto remove excess phosphorus oxychloride
- customthe residue triturated with ice-water
- extractionThe resultant aqueous solution was extracted with methylene chloride
- customthe organic layer thus obtained
- customwas dried
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-dc67e3fed2b944e0a9e53b2ee088e8b8
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238653B2
Reaction notes
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