Synthesis of a Transition State Analogue Inhibitor of Purine Nucleoside Phosphorylase via the Mannich Reaction

[reaction: see text] The expeditious convergent synthesis of the potent human purine nucleoside phosphorylase inhibitor DADMe-Immucillin-G (3) was achieved via the Mannich reaction. The Mannich chemistry of a series of deazapurines and amine hydrochlorides was also investigated.