4,4,4-Trifluoro-1-(4-trifluoromethylphenyl)-1,3-butanedione → 3-Bromo-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 558539Notes

Reaction equation

HRID 558539 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[CH:5][NH:4][N:3]=1.[F:8][C:9]([F:26])([F:25])[C:10](=O)[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=O>C(O)(=O)C.O>[Br:7][C:6]1[CH:5]=[N:4][N:3]2[C:10]([C:9]([F:8])([F:26])[F:25])=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=3)=[N:1][C:2]=12

Participants

5

Reactant 2

HCID 108590204,4,4-Trifluoro-1-(4-trifluoromethylphenyl)-1,3-butanedioneHCID 178509245HCID 178509245, compound

Product 1

HCID 715396793-Bromo-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidineYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A stirred mixture of commercially available 3-amino-4-bromo-pyrazole (14.00 g, 86.4 mmol) and 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (Example C.1 step 1) (24.56 g, 86.4 mmol) in acetic acid (170 mL) was heated under reflux conditions for 2.5 h. The reaction mixture was cooled to room temperature, diluted with water (340 mL), the precipitate was filtered off, washed with water and dried in air at 60° C. to give the 3-bromo-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (31.77 g, 90%) as a yellow solid. MS (EI) 410.0 [(M)+], 412.0 [(M+2)+]; mp 136° C.

Workup

  1. temperaturewas heated under reflux conditions for 2.5 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried in air at 60° C.

Sources & evidence

ORD record
ord-35bc5fcb7b03488cbbcc9a17e8ef2443
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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