N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide → 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime

Participants

Reaction Conditions

Reaction Steps

A solution of N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (563.4 mg, 1.93 mmol) in dioxane (5.8 mL) and hydrazine monohydrate (9.6 mL) was heated under reflux for 48 h. The reaction mixture was allowed to cool to 25° C. and then was diluted with ethyl acetate (100 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/7 ethyl acetate/hexanes) afforded 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime (408.4 g, quant.) as a light yellow solid: mp 113–115° C.; EI-HRMS m/e calcd for C10H16N4O (M+) 208.1324, found 208.1325.

Provenance & Evidence