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

HRID 2054309Notes

Reaction equation

HRID 2054309 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[N:27]=[CH:28][NH:29][C:30]=1[C:31]#[N:32]>>[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[CH:28]=[N:29][C:30]([C:31]#[N:32])=[C:26]2[N:25]=1

Participants

4

Reactant 3

HCID 142862-AcetylpyridineHCID 787775-amino-1H-imidazole-4-carbonitrileHCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione

Product 1

HCID 672133522-Pyridin-2-yl-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-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 4-amino-5-cyano-1H-imidazole (108 mg, 1.0 mmol) according to general procedure B yielded the title compound as a yellow solid (135 mg, 47%). MS (ISP) 289.9 [(M+H)+]; mp 205° C.

Sources & evidence

ORD record
ord-a09147441c5b43728e8271431cf7dfe3
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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