Hydrochloric Acid → 6-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one

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To an solution of 6-(2-chloro-5-nitrophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one (73.2 mmol) in EtOH (700 mL) were added conc. aq. hydrochloric acid (170 mL) and iron powder (732 mmol), and the mixture was stirred at 80° C. for 6 h. The mixture was allowed to cool to room temperature and filtered through a pad of Celite. The filtrate was diluted with EtOAc (700 mL) and washed with sat. aq. NaHCO3 (700 mL). The aqueous layer was backextracted with EtOAc (8×300 mL). The organic layers were combined and washed with sat. aq. NaCl (1×700 mL). Drying of the organic layer over Na2SO4, followed by evaporation of the solvent gave crude product that was purified by column chromatography on silica gel (dichloromethane/triethylamine 95:5, followed by dichloromethane/MeOH/triethylamine 90:5:5). The collected fractions were dissolved in dichloromethane and washed with water to remove triethylamine salts. The aqueous layer was backextracted with dichloromethane, the organic layers were combined, dried over Na2SO4, filtered and evaporated to give 6-(5-amino-2-chlorophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one as a solid (32%).

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