Hydrogen Bromide → 4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-bromo-pyrido[2,3-d]pyrimidine

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4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-amino-pyrido[2,3-d]pyrimidine (1.45 g; 4 mmol) and cuprous bromide (1.15 g; 8 mmol) was dissolved in a mixture of water (25 mL) and concentrated hydrobromic acid (25 mL). The solution was chilled in an ice bath, and to it was added sodium nitrite (340 mg; 5 mmol, in aqueous solution). The solution was stirred for ten minutes, and then heated to 60° C. for one hour. It was then poured into a 10% solution of potassium carbonate, and extracted with dichloromethane (2×50 mL). The organic layer was dried over magnesium sulfate, evaporated, and the product was purified by column chromatography to give 4-morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-bromo-pyrido[2,3-d]pyrimidine (0.98 g).

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