Diisopropylethylamine → 5-Furan-2-yl-pyrazin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-5-bromopyrazine (500 mg, 2.87 mmol) in N,N-dimethylformamide (15 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (66 mg, 0.06 mmol), N,N-diisopropylethylamine (1.25 mL, 7.18 mmol), lithium chloride (426 mg, 10.06 mmol), and 2-(tributylstannyl)furan (905 μL, 2.87 mmol). The resulting reaction mixture was heated at 120° C. for 4 h. After such time, the reaction was cooled to 25° C., treated with a saturated aqueous potassium fluoride solution (10 mL), and then stirred at 25° C. overnight for 16 h. The solution was then diluted with methylene chloride (25 mL) and extracted with methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 98/2 to 96/4 methylene chloride/methanol) afforded 5-furan-2-yl-pyrazin-2-ylamine (356 mg, 77%) as a brown solid: mp 80.2–83.8° C.

Provenance & Evidence