Cesium fluoride → 4-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

To 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1.34 g, 5.59 mmol) was added DMF (8 mL), dioxane (48 mL), cesium fluoride (2.55 g, 16.78 mmol), X-Phos (0.258 g, 0.559 mmol), palladium (II) acetate (0.126 g, 0.559 mmol), and tributyl(1-ethoxyvinyl)stannane (2.64 mL, 7.83 mmol) (Aldrich), and the resulting mixture was stirred at 110° C. for 1.5 h. The reaction mixture was cooled to ambient temperature and purified via flash chromatography (neutral alumina) with 100% DCM (to remove the stannane), then 100% EtOAc to give the title compound (>99% yield). m/z (ESI, +ve ion) 276.0 (M+H)+.

Provenance & Evidence