3-Acetylpyridine → 2-Pyridin-3-yl-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 2108486

Reaction equation

HRID 2108486 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])[CH:2]=1.C(C1C=NC=CC=1)(=O)C.[NH2:25][C:26]1[N:27]=[CH:28][NH:29][C:30]=1[C:31]#[N:32]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[N:27]3[CH:28]=[N:29][C:30]([C:31]#[N:32])=[C:26]3[N:25]=2)[CH:2]=1

Participants

4

Reactant 3

HCID 95893-AcetylpyridineHCID 684951,3-Butanedione, 4,4,4-trifluoro-1-(3-pyridinyl)-HCID 787775-amino-1H-imidazole-4-carbonitrile

Product 1

HCID 672131042-Pyridin-3-yl-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrileYield 13%

Procedure

Reaction of 1-pyridin-3-yl-4,4,4-trifluoro-butane-1,3-dione (217 mg, 1.0 mmol), prepared from commercially available 3-acetylpyridine according to general procedure A, and 4-amino-5-cyano-1H-imidazole (108 mg, 1.0 mmol) according to general procedure B yielded the title compound as a yellow solid (37 mg, 13%). MS (ISP) 290.1 [(M+H)+]; mp 222° C.

Sources & evidence

ORD record
ord-6ebc45b278444504b9eadec38845f056
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Linked notes

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