Pyridine → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 1447870Notes

Reaction equation

HRID 1447870 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]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 146774714-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Product 1

HCID 157125564-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. additionA mixture of 2.0 g
  2. additionTo this is added 1.51 g
  3. filtrationthe resulting solid is collected by filtration
  4. dissolutionThis solid is dissolved in methylene chloride
  5. temperatureThe effluent is refluxed with the continued addition of hexane until crystallization
  6. temperatureCooling
  7. customgives the desired solid product which
  8. filtrationis recovered by filtration, m.p. 168°-169° C.

Sources & evidence

ORD record
ord-2cb68af7f99140818ed5bdb9ef348d88
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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