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

HRID 268980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268980
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8e0f9f7d6cb24203af5c698fa1c48bcd
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446113B2

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