Sodium Acetate → 5-(alpha,alpha,alpha-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

HRID 225287Notes

Reaction equation

HRID 225287 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:12]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:15][CH:16]=2)[CH:3]=1.C([O-])(=O)C.[Na+].[H][H]>[Pd]>[F:19][C:17]([F:18])([F:20])[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:4]2[CH:3]=[CH:2][N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 233298597-Chloro-5-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 112308145-(alpha,alpha,alpha-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The mixture of 1.65 g. 7-chloro-5-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine, 0.46 g. of anhydrous sodium acetate, 0.20 g. of 10% palladium on charcoal catayst and 100 ml. of absolute alcohol is hydrogenated in a Parr apparatus beginning at 10 lbs. pressure until one equivalent of hydrogen is absorbed in about 40 minutes. The catalyst is removed by filtration and the solvent is evaporated to dryness and water is added. The solid is collected by filtration and is recrystallized from methylene chloride-hexane to yield the desired material, m.p. 117°-118° C.

Workup

  1. additionThe mixture of 1.65 g
  2. customThe catalyst is removed by filtration
  3. customthe solvent is evaporated to dryness and water
  4. additionis added
  5. filtrationThe solid is collected by filtration
  6. customis recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-1fef6677952349fbb4a1cc288e37a229
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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