Dimethylformamide → 2-(5-Aminopyrazin-2-ylthio)ethanol

Participants

Reaction Conditions

Reaction Steps

Based on the method described in WO2004/052869, mercaptoethanol (0.93 mL) and tetrakis(triphenylphosphine)palladium (3.39 g) were added to a solution of 1.00 g of 2-amino-5-bromopyrazine (5.75 mmol) in N,N-dimethylformamide (15.1 mL), and the resulting mixture was heated and stirred in a sealed tube for about 3 hours at 120° C. After cooling, the reaction mixture was diluted with water, and then extracted (100 mL×6) with a mixed liquid (methylene chloride:ethanol=5:1). The organic layer was dried over anhydrous sodium sulfate, then filtered, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate, and then ethyl acetate:methanol=10:1), then recrystallized (chloroform) to obtain 470 mg of the title compound (yield 44%) as yellow needle-like crystals.

Provenance & Evidence