3-Bromo-1-propanol → 2-adamantan-1-yl-N-[7-(3-hydroxy-propyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-acetamide

A solution of 2-adamantan-1-yl-N-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide (0.05 g, 0.153 mmol), 3-bromo-1-propanol (0.021 g, 0.15 mmol) and DIPEA (0.045 g, 0.35 mmol) in EtOH (4 mL) was stirred at 75° C. for 17 h. The reaction vessel was allowed to cool to room temperature, opened, and the volatiles were removed on a rotary evaporator. The residue was redissolved in THF (3 mL). PL-NCO resin (300 mg) was added, and the resulting suspension was stirred at room temperature for 16 h. The resin was filtered and the volatiles were removed under vacuum. The crude product was purified by HPLC to afford 2-adamantan-1-yl-N-[7-(3-hydroxy-propyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-acetamide (0.0098 g, 17%).