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

HRID 2108394Notes

Reaction equation

HRID 2108394 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[CH:5][CH:4]=1.[NH2:20][C:21]1[C:25]([C:26]#[N:27])=[CH:24][NH:23][N:22]=1>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:22]3[N:23]=[CH:24][C:25]([C:26]#[N:27])=[C:21]3[N:20]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 108590204,4,4-Trifluoro-1-(4-trifluoromethylphenyl)-1,3-butanedioneHCID 178510443HCID 178510443, compound

Product 1

HCID 114055925-(4-Trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 38.5%

Procedure

Reaction of 1-(4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (284 mg, 1.0 mmol), prepared from commercially available 4-trifluoromethyl-acetophenone according to general procedure A, and 3-amino-4-cyano-pyrazole (108 mg, 1.0 mmol) according to general procedure B yielded the title compound as an off-white solid (137 mg, 38%). MS (ISP) 357.0 [(M+H)+]; mp 176° C.

Sources & evidence

ORD record
ord-8cfaa7fd45db42d4a2ef41d28ab8b490
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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