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

HRID 558559Notes

Reaction equation

HRID 558559 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=O.[NH2:20][C:21]1[CH:25]=[CH:24][NH:23][N:22]=1>C(O)(=O)C>[F:14][C:13]([F:16])([F:15])[C:9]1[CH:8]=[C:7]([C:5]2[CH:4]=[C:3]([C:2]([F:19])([F:18])[F:1])[N:22]3[N:23]=[CH:24][CH:25]=[C:21]3[N:20]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 162279574,4,4-Trifluoro-1-[3-(trifluoromethyl)phenyl]butane-1,3-dioneHCID 178418806HCID 178418806, compound

Product 1

HCID 866079975-(3-Trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 95.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4,4,4-trifluoro-1-(3-trifluoromethyl-phenyl)-butane-1,3-dione (10.3 g, 36.1 mmol) and commercially available 3-aminopyrazole (3.0 g, 36.1 mmol) in acetic acid (100 mL) was refluxed for 4 h and evaporated. The crude product was further purified by crystallization (ethyl acetate/hexane) to yield 5-(3-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (11.4 g, 95%) as a light yellow solid. MS (ISP) 323.3 [(M+H)+]; mp 96° C.

Workup

  1. temperaturewas refluxed for 4 h
  2. customevaporated
  3. customThe crude product was further purified by crystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eba26dc1ac9d4694ac2d7c22727ce5c5
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

Loading…