A NEW SYNTHETIC ROUTE TO 2-DEUTERIOADENINES SUBSTITUTED OR UNSUBSTITUTED AT THE 9-POSITION

Article abstract of DOI:10.3987/R-1986-09-2449

9-alkyl-2-deuterioadenines (VIII b-d) , adenosine-2-d (VIIIe), and 2'-deoxyadenosine-2-d (VIIIf) were synthesized from the 9-substituted adenines Ib-f through cyclization of the monocyclic intermediates VIb-f with formic acid-d2 or 1-(formyl-d)-2-(1H)-pyridone.Hydrolysis of VIIIe, prepared through this synthetic route, with 0.5 N aqueous HCl ( reflux, 2h) gave adenine-2-d (VIIIa) in 77percent yield.Unambiguous assigments of the purine ring protons in the NMR spectra of the unlabeled adenines Ia-f have been made by comparison with those of the labeled adenines VIIIa-f.