2-Aminopyridine → 4-(2-chloro-4-pyrimidinyl)-N-(3-fluorophenyl)-2-pyridinamine

Participants

Reaction Steps

To a solution of N-(3-fluorophenyl)-4-trimethylstannyl)-2-pyridinamine (i.e., the product of Step B) (4.0 g, 11 mmol) in 1,4-dioxane (100 mL) under nitrogen was added 2,4-dichloropyrimidine (2.26 g, 15 mmol), copper iodide (216 mg, 1.1 mmol) and bis(triphenylphosphine)palladium(II) dichloride (400 mg, 0.57 mmol). The resulting mixture was stirred at reflux for 4 h. After cooling to room temperature, the solution was concentrated under reduced pressure. The resulting residue was purified using column chromatography on silica gel eluted with 25% ethyl acetate in hexanes to afford 2.3 g of title compound as a yellow solid.

Provenance & Evidence