Phosphorus oxychloride → 7-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1447888Notes

Reaction equation

HRID 1447888 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[N:15]=[CH:16][C:17]([C:18]([NH2:20])=O)=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.P(Cl)(Cl)(Cl)=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[N:15]=[CH:16][C:17]([C:18]#[N:20])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27776927-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 27410147-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Procedure

One gram of 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide and 5 ml. of phosphorus oxychloride is refluxed for 3 hours. The reaction mixture is evaporated to dryness and the residue is dissolved in methylene chloride, washed with saturated sodium bicarbonate solution, dried with anhydrous sodium sulfate. After passing through a short pad of hydrous magnesium silicate with eluent methylene chloride. Concentration of the eluent with addition of n-hexane gives the product, m.p. 141°-143° C.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutionthe residue is dissolved in methylene chloride
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. additionConcentration of the eluent with addition of n-hexane
  6. customgives the product, m.p. 141°-143° C.

Sources & evidence

ORD record
ord-67ede502dbfe46ea9f2258b8197708ba
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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