4-Aminopyridine → 2-(5-Bromo-2-fluorophenyl)-4-(4-pyridylamino)pteridine

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Reaction Steps

Triethylamine (1.04 mL, 7.17 mmol) was added to a solution of 2-(5-bromo-2-fluoro-phenyl)pteridin-4-one 104 (800 mg, 2.49 mmol), 4-aminopyridine (469 mg, 4.98 mmol) and PyBOP (2.59 g, 4.98 mmol) in CH2Cl2. After 12 h, the reaction mixture was partitioned between CH2Cl2/Petroleum ether (2:1, 300 mL) and ice-cold 1N HCl (300 mL). The pH of the water phase was adjust to 12 with conc. NaOH and extracted with AcOEt, dried (Na2SO4) and evaporated. The residue was triturated in CH2Cl2/Petroleum ether (2:1, 15 mL), filtered off, and washed with ether. The product was purified by column chromatography (AcOEt/CH2Cl2/MeOH, 5:4:1) to give 325 mg of the title product 1 as a yellow powder (LCMS analysis).

Provenance & Evidence