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 1293745Notes

Reaction equation

HRID 1293745 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 670008454-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl esterYield 49.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-497b60418fd24eb193d1296861f1f041
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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