Dimethylformamide → 7-(alpha,alpha,alpha-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxaldehyde

HRID 1447909Notes

Reaction equation

HRID 1447909 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]([F:24])([F:23])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:19]3[N:20]=[CH:21][CH:22]=[C:18]3[N:17]=[CH:16][CH:15]=2)[CH:9]=1.[OH-].[Na+].CN(C)[CH:29]=[O:30]>>[F:24][C:7]([F:23])([F:6])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:19]3[N:20]=[CH:21][C:22]([CH:29]=[O:30])=[C:18]3[N:17]=[CH:16][CH:15]=2)[CH:9]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 197562037-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine

Product 1

HCID 233298407-(alpha,alpha,alpha-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxaldehyde

Procedure

Seventy-five milliliters of dried dimethylformamide is cooled in an ice bath and 25 ml. of phosphorus oxychloride is added dropwise with swirling. To this ice cold mixture is added 19.5 g. of 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine in one portion and the reaction mixture is then heated on a steam bath for 1.5 hours. The mixture is poured onto ice and made basic (pH 10) with 10 N NaOH. The precipitated solid is removed by filtration and recrystallized from methylene chloride-hexane to give the product, m.p. 196° 198° C.

Workup

  1. additionThe mixture is poured onto ice
  2. customThe precipitated solid is removed by filtration
  3. customrecrystallized from methylene chloride-hexane
  4. customto give the product, m.p. 196° 198° C.

Sources & evidence

ORD record
ord-d7d0a5ac5f054e199ae96d9c43dfabae
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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