Adenine → 2-chloro-N-(3-iodobenzyl)-7H-purin-6-amine

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N6 -(3-iodobenzyl)-2-substituted adenosine derivatives can be synthesized from the corresponding adenine derivative. 2,6-Dichloropurine reacted with 3-iodobenzylamine hydrochloride in the presence of triethylamine in ethanol at room temperature provides N6 -(3-iodobenzyl)-2-chloroadenine, which can be silylated before coupling to yield the silylated derivative. The glycosidic bond is formed upon treatment of the 1'-O-acetyl riboside derivative N-methyl 1-O-acetyl-2,3-dibenzoyl-β-D-ribofuronamide with the aforesaid 9-silylated adenine derivative in the presence of TMSOTf as a Lewis acid catalyst. Condensation of N-methyl 1-O-methyl-2,3-dibenzoyl-β-D-ribofuronamide with the aforesaid 9-silylated adenine derivative produces ribose ring-opened product. Benzoyl groups of 2-chloro-N6 -(3-iodobenzyl)-9-[5-(methylamido)-2,3-di-O-benzoyl-β-D-ribofuranosyl]-adenine are deprotected with NH3 /MeOH to produce 2-chloro-N6 -(3-iodobenzyl)-9-[5-(methylamido)-β-D-ribofuranosyl]-adenine, which reacted with various nucleophiles such as methylamine/THF and sodium thiomethoxide/DME yield compounds N6 -(3-iodobenzyl)-2-methylamino-9-[5-(methylamido)-β-D-ribofuranosyl]-adenine and N6 -(3-iodobenzyl)-2-methylthio-9-[5-(methylamido)-β-D-ribofuranosyl]-adenine. The benzoyl groups of 2-chloro-N6 -(3-iodobenzyl)-9-[2,3,5-tri-O-benzoyl-β-D-ribofuranosyl]-adenine can be similarly deprotected to produce the riboside derivative 2-chloro-N6 -(3-iodobenzyl)-9-[β-D-ribofuranosyl]-adenine.

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