1,8-Diazabicyclo(5.4.0)undec-7-ene → 5,7-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrimidine

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Reaction Conditions

Reaction Steps

A mixture of 3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazole-5-carbaldehyde (54 mg, 218 μmol, Eq: 1.00), ((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (99.8 mg, 218 μmol, Eq: 1.00) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (82.8 mg, 544 μmol, Eq: 2.5) in tetrahydrofuran (3.36 ml) was stirred for 18 hours at 25° C. under argon atmosphere. Chromatography afforded 5,7-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-a]pyrimidine (20 mg/23.4%) as a light yellow viscous oil. MS: m/z=393.4 (M+H+).

Provenance & Evidence