1,8-Diazabicyclo(5.4.0)undec-7-ene → Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(cyclopropyl(methyl)amino)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde (45 mg, 250 μmol, Eq: 1.00) in tetrahydrofuran (2.3 ml) were added ((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (115 mg, 250 μmol, Eq: 1.00) and DBU (95.0 mg, 94.1 μl, 624 μmol, Eq: 2.5). The resulting mixture was stirred for 18 hours at 25° C. TLC (Hep/EtOAC 1:1/UV 254 nm) showed no starting material left and new product spot. MS showed product peak also. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 1:1 as eluent to give Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine (30 mg, 37%) as light yellow waxy solid

Provenance & Evidence