Adenine → 9-((2-(2-Chlorophenyl)-8-methylquinolin-3-yl)methyl)-9H-purin-6-amine

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Reaction Steps

A mixture of 3-(bromomethyl)-2-(2-chlorophenyl)-8-methylquinoline (66 mg, 0.19 mmol), {prepared in a similar way as 3-(bromomethyl)-8-methyl-2-o-tolylquinoline, example 9} adenine (39 mg, 0.29 mmol), and cesium carbonate (124 mg, 0.38 mmol) in DMF (0.7 mL) was stirred at rt for 2 h. The crude mixture was evaporated onto silica gel and purified by flash chromatography (Biotage Si 25+M) eluting with MeOH/CH2Cl2 (5% to 10%). The resulting white solid was further purified by HPLC (Berger SFC) eluting with i-PrOH/CO2/DEA to provide a white solid [PI3Kδ IC50=2130 nM]. MS (ESI+) m/z=401.1 (M+1).

Provenance & Evidence