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

HRID 2054307Notes

Reaction equation

HRID 2054307 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12](=O)[CH2:13][C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[NH2:21][C:22]1[N:23]=[CH:24][NH:25][C:26]=1[C:27]#[N:28]>>[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[N:23]3[CH:24]=[N:25][C:26]([C:27]#[N:28])=[C:22]3[N:21]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]

Participants

3

Reactant 2

HCID 787775-amino-1H-imidazole-4-carbonitrileHCID 86598668HCID 86598668, compound

Product 1

HCID 114741622-(3-Methyl-4-trifluoromethyl-phenyl)-4-trifluoromethyl-imidazo[1,5-a]pyrimidine-8-carbonitrileYield 47.2%

Procedure

Reaction of 1-(3-methyl-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (224 mg, 0.75 mmol), prepared from 3-methyl-4-trifluoromethyl-acetophenone (synthesis: see part acetophenone derivatives) according to general procedure A, and 4-amino-5-cyano-1H-imidazole (81 mg, 0.75 mmol) according to general procedure B yielded the title compound as a yellow solid (131 mg, 47%). MS (ISP) 371.1 [(M+H)+]; mp 217° C.

Sources & evidence

ORD record
ord-af3bb8e7d1194eafa76b630e1cd950c0
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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