Ammonium Chloride → 7-Methyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 558565Notes

Reaction equation

HRID 558565 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:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:3]=1.[CH3:21][Zn]C.C1(C)C=CC=CC=1.[NH4+].[Cl-]>C1COCC1>[CH3:21][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866080007-Chloro-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidineHCID 178424248HCID 178424248, compound

Product 1

HCID 670009317-Methyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidineYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (1.49 g, 5.0 mmol) and tetrakis(triphenylphosphin)palladium (1.73 g, 1.5 mmol) in THF (50 mL) was added at 20° C. 2 M dimethylzinc/toluene solution (6.25 mL, 12.5 mmol) and the mixture was refluxed in an atmosphere of argon for 2 h. After the slow addition at 0° C. of sat. aqueous NH4Cl solution (12 mL), the mixture was partitioned between AcOEt and 10% sodium chloride solution. The organic layer was evaporated in vacuo and the residue was chromatographed on silica gel using AcOEt/hexane (1:3 v/v) as eluent to give the title compound (1.17 g, 84%). Pale yellow solid. MS (ISN) 276.1 [(M−H)−]; mp 89-90° C.

Workup

  1. customthe mixture was partitioned between AcOEt and 10% sodium chloride solution
  2. customThe organic layer was evaporated in vacuo
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-20b5df8a501942faaf563320ddc82737
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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