Pyridine → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([NH2:20])=O)=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.N1C=CC=CC=1.O1CCOCC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]#[N:20])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2.0 g. of 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide, 1.03 g. of anhydrous pyridine and 50 ml. of anhydrous dioxane is chilled in an ice bath. To this is added 1.51 g. of trifluoroacetic anhydride and the mixture is stirred at room temperature overnight. Water is added and the resulting solid is collected by filtration. This solid is dissolved in methylene chloride and passed through a column of hydrous magnesium silicate. The effluent is refluxed with the continued addition of hexane until crystallization is started. Cooling gives the desired solid product which is recovered by filtration, m.p. 168°-169° C.
Workup
- additionA mixture of 2.0 g
- additionTo this is added 1.51 g
- filtrationthe resulting solid is collected by filtration
- dissolutionThis solid is dissolved in methylene chloride
- temperatureThe effluent is refluxed with the continued addition of hexane until crystallization
- temperatureCooling
- customgives the desired solid product which
- filtrationis recovered by filtration, m.p. 168°-169° C.
Sources & evidence
- ORD record
- ord-c794d928da40486d8be89b5f32014ffa
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04236005
Reaction notes
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