Ethyl chloroformate → ethyl pyrido[3,4-b]pyrazine-6(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of pyrido[3,4-b]pyrazine (20.0 g, 153 mmol) in anhydrous THF (250 mL) is cooled to −25° C. A solution of ethyl chloroformate (17.5 ml, 183 mmol) in THF (46 mL) is added dropwise. The mixture is stirred 1 hr at −25° C., and then LiBH4 (2.0 M, 23 mL, 46 mmol) is added dropwise and the mixture is stirred for 1 hr. The reaction is quenched with the addition of 1N NaOH (100 mL) and extracted with Et2O (3×100 mL). The organic extractions are combined, dried and evaporated. The crude product is purified by silica gel column chromatography eluting with hexane/EtOAc (3:2) to yield the title compound. MS (+VE) m/z 206.14 (M++1).

Provenance & Evidence