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

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Reaction Conditions

Reaction Steps

A mixture of ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (125 mg, 272 μmol, Eq: 1.00), 1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (52.9 mg, 272 μmol, Eq: 1.00) and 1,8-diazabicyclo[5.4.0]undec-7-ene (104 mg, 103 μl, 681 μmol, Eq: 2.5) in tetrahydrofuran (6 ml) was stirred for 18 hours at 25° C. under nitrogen atmosphere. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using ethyl acetate methanol 0-10% as eluent affording 2-[2-(2-ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (37 mg/40.1%) as a bright yellow viscous oil. MS: m/e=339.5 (M+H+)

Provenance & Evidence