4,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione → 4-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester

HRID 1293745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1293745
[F:1][CH:2]([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.[CH2:19]([O:21][C:22]([C:24]1[N:25]=[CH:26][NH:27][C:28]=1[NH2:29])=[O:23])[CH3:20]>C(O)(=O)C>[CH2:19]([O:21][C:22]([C:24]1[N:25]=[CH:26][N:27]2[C:3]([CH:2]([F:18])[F:1])=[CH:4][C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)=[N:29][C:28]=12)=[O:23])[CH3:20]

Komponenten

4

Edukt 2

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dioneHCID 178470302HCID 178470302, Verbindung

Produkt 1

HCID 670008454-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl esterAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 4,4-difluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (8.87 g, 33.3 mmol) and 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (5.17 g, 33.3 mmol) in acetic acid (100 ml) was refluxed for 27h and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) and crystallization (diethyl ether/hexane) to yield 4-difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (6.35 g, 49%) as a yellow solid. MS (EI) 385.1 [(M)+]; mp 219° C.

Aufarbeitung

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) and crystallization (diethyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-497b60418fd24eb193d1296861f1f041
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238808B2

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