Cesium carbonate → 6-Pyridin-3-yl-5-pyridin-4-yl-N-1,3-thiazol-2-ylpyrazin-2-amine

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Reaction Steps

An oven dried resealable Schlenk tube was charged with 6-pyridin-3-yl-5-pyridin-4-ylpyrazin-2-amine (Example 13, 60 mg, 0.241 mmol), 2-bromo-1,3-thiazole (22 μL, 0.241 mmol), cesium carbonate (110 mg, 0.337 mmol) and dioxane (2.5 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.01 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (11 mg, 0.019 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 16 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (95:5 dichloromethane/methanol) furnished the title compound as a solid (35 mg, 44%).

Provenance & Evidence