Syntheses of [6,7-15N]-adenosine, [6,7-15N]-2'-deoxyadenosine, and [7-15N]-hypoxanthine

Article abstract of DOI:10.1021/ja00152a006

We have developed a high-yield route for the synthesis of [7-¹⁵N]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [¹⁵N]-sodium nitrite as the ¹⁵N source and an inexpensive pyrimidine to provide an economical route to this useful ¹⁵N-labeled intermediate. Conversion to [7-¹⁵N]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2'-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-¹⁵N]-labeled nucleosides is effected simply and in high yield using 2 equiv of [¹⁵N]-ammonium chloride and 3 equiv of potassium bicarbonate.