2-Methylfuran → 6-(5-Methylfuran-2-yl)-5-phenylpyrazin-2-ylamine

Participants

Reaction Steps

An oven dried resealable Schlenk tube was charged with 6-chloro-5-pyridin-4-ylpyrazin-2-amine (Preparation 7, 300 mg, 1.45 mmol), 2-methylfuran (1.31 mL, 14.5 mmol), potassium acetate (213 mg, 2.17 mmol) and N,N-dimethylacetamide (6 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium (117 mg, 0.10 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 150° C. oil bath. After 40 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted with ethyl acetate (×3), the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane/methanol 98:2 to dichloromethane/methanol 90:10) furnished the title compound as a brown solid (45 mg, 12%).

Provenance & Evidence