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Crystal Structure of cis-4,5-Dimethoxy-1,3-dimethyl-tetrahydropurine-2,6,8-trione, C9H14N4O5

Two independent molecules of the title compound adopt the ring-twisted conformation (b), defined by roughly orthogonal bridgehead torsion angles (N13-C14-C15-N17 = 95.1(3) and N23-C24-C25-N27 = 97.1(3)degrees). Stereoelectronically controlled ring-opening at the N3-C4 bond in the course of acidic hydrolysis thus occurs at the acid aminal stage of the multistep reaction [ref. 4] via a conformational change to the proper ring-twisted conformer (a).

oxidative transformations; purines; uric acid; uricolysis; covalent adducts; ethers; stereoelectronic control.

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