1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90026195, compound

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Reaction Conditions

Reaction Steps

A mixture of 1-methyl-3-(piperidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (60 mg, 309 μmol, Eq: 1.00), ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (142 mg, 309 μmol, Eq: 1.00) and DBU (51.7 mg, 51.2 μl, 340 μmol, Eq: 1.1) in tetrahydrofuran (15 ml) was stirred for 18 hours at 25° C. under argon. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using ethyl acetate/methanol 0-7% as eluent affording 5,8-dimethyl-2-[(E)-2-(2-methyl-5-piperidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-[1,2,4]triazolo[1,5-a]pyrazine (56 mg, 53.6%) as a yellow solid. MS: m/z=339.5 (M+H+), MP: 186-188° C.

Provenance & Evidence