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

HRID 2108487Notes

Reaction equation

HRID 2108487 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:3][CH:2]=1.C(C1C=CN=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][C:4]([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:3][CH:2]=1

Participants

4

Reactant 3

HCID 142824-AcetylpyridineHCID 787775-amino-1H-imidazole-4-carbonitrileHCID 2382984,4,4-Trifluoro-1-(pyridin-4-yl)butane-1,3-dione

Product 1

HCID 672129912-Pyridin-4-yl-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrileYield 27%

Procedure

Reaction of 1-pyridin-4-yl-4,4,4-trifluoro-butane-1,3-dione (217 mg, 1.0 mmol), prepared from commercially available 4-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 (77 mg, 27%). MS (ISP) 289.8 [(M+H)+]; mp 254° C.

Sources & evidence

ORD record
ord-cc4a8246a57842fd9f6332a957ebac62
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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