Potassium tert-butoxide → 2-bromo-5H-pyrrolo[2,3-b]pyrazine

Participants

Reaction Conditions

Reaction Steps

To a 250 ml three necked round bottom flask, potassium tert-butoxide (4.2 g, 0.037 mole) was taken in THF (50 ml). To this, 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (10.0 g, 0.037 mole) in THF (50 ml) was added dropwise at RT over 20 min under nitrogen atmosphere and the reaction mixture was stirred for 30 min at same temperature and 60 min at 65° C. The completion of the reaction was monitored by TLC using hexanes:ethyl acetate (8:2) as a mobile phase. After completion of the reaction, the reaction mixture was cooled to RT and diluted with ethyl acetate, filtered through high flow. Filtrate was collected and washed with water. The layers were separated and the aq. layer was re-extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, filtered, and concentrated to afford crude product which was subjected for the column purification. The crude compound was purified using column purification by eluting the compound with 15-20% ethyl acetate in hexanes to yield 4.3 g of 2-bromo-5H-pyrrolo[2,3-b]pyrazine.

Provenance & Evidence