To a solution of 1 mmol 1-(1-benzyl-piperidin-4-yl)-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine dissolved in EtOH (10 mL) was added 1 mmol 8-oxa-3-aza-bicyclo[3.2.1]octane, (Newth, F. H. and Wiggins, L. F. Journal of the Chemical Society. 1948, pages 155-158) prepared from 1,5-hexadiene by the four-step process of RuCl3-catalyzed NaIO4 oxidation, conversion to the bis tosylate, cyclization with benzyl amine, and deprotection with 1-chloroethyl chloroformate followed by methanol (Scheme 46). The reaction was stirred for 18 h. The solvents were evaporated and the reminder was triturated with diethyl ether/hexane. The solid was filtered off and washed with hexane. Drying on the fritted funnel provided a solid.
