5-amino-1H-imidazole-4-carbonitrile → 2-(4-Methyl-3-trifluoromethyl-phenyl)-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 2054306Notes

Reaction equation

HRID 2054306 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].[NH2:21][C:22]1[N:23]=[CH:24][NH:25][C:26]=1[C:27]#[N:28]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:23]3[CH:24]=[N:25][C:26]([C:27]#[N:28])=[C:22]3[N:21]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

3

Reactant 2

HCID 787775-amino-1H-imidazole-4-carbonitrileHCID 865986651-(4-Methyl-3-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione

Product 1

HCID 113721262-(4-Methyl-3-trifluoromethyl-phenyl)-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrileYield 39%

Procedure

Reaction of 1-(4-methyl-3-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (298 mg, 1.0 mmol), prepared from 4-methyl-3-trifluoromethyl-acetophenone (synthesis: see part acetophenone derivatives) 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 (143 mg, 39%). MS (ISP) 371.1 [(M+H)+]; mp 220° C.

Sources & evidence

ORD record
ord-ac431ddc1b3844909cf16a2f1d81fb27
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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