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

HRID 2237843Notes

Reaction equation

HRID 2237843 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[NH2:20][C:21]1[CH:25]=[CH:24][NH:23][N:22]=1>C(O)(=O)C>[F:1][C:2]([F:19])([F:18])[C:3]1[N:22]2[N:23]=[CH:24][CH:25]=[C:21]2[N:20]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 108590204,4,4-Trifluoro-1-(4-trifluoromethylphenyl)-1,3-butanedioneHCID 178418806HCID 178418806, compound

Product 1

HCID 715397317-(Trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidineYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (Example C.1, method 1, step 1) (2.84 g, 10 mmol) and 3-aminopyrazole (0.83 g, 10 mmol) in acetic acid (20 mL) were refluxed for 4 h. The reaction mixture was cooled to rt and poured into ice water (200 mL), extracted with EtOAc, dried over MgSO4, filtered and concentrated, and triturated with toluene, and dried to give 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (3.28 g, 99%) as a yellow solid. MS (ISP) 332.1 [(M+H)+]; mp 110-111° C.

Workup

  1. temperaturewere refluxed for 4 h
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customtriturated with toluene
  7. customdried

Sources & evidence

ORD record
ord-d42adc62e63b48b1985d5a774594ab23
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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