2-Acetylpyridine → 5-Pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2108405Notes

Reaction equation

HRID 2108405 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11].C(C1C=CC=CN=1)(=O)C.[NH2:25][C:26]1[C:30]([C:31]#[N:32])=[CH:29][NH:28][N:27]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[N:27]2[N:28]=[CH:29][C:30]([C:31]#[N:32])=[C:26]2[N:25]=1

Participants

4

Reactant 3

HCID 142862-AcetylpyridineHCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dioneHCID 178510443HCID 178510443, compound

Product 1

HCID 458345455-Pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 47%

Procedure

Reaction of 1-pyridin-2-yl-4,4,4-trifluoro-butane-1,3-dione (217 mg, 1.0 mmol), prepared from commercially available 2-acetylpyridine 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 a light brown solid (135 mg, 47%). MS (ISP) 289.9 [(M+H)+]; mp 208° C.

Sources & evidence

ORD record
ord-c06cfa76557b4b1ebbdd6e942f5d0fa6
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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