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Synthesis of morpholinium [ 13 C] formate and its application in the synthesis of [8‐ 13 C] purine base
Author(s) -
Sharma Minoti,
Alderfer James L.,
Box Harold C.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580201013
Subject(s) - chemistry , formate , morpholine , yield (engineering) , sodium formate , base (topology) , medicinal chemistry , guanine , aqueous solution , inorganic chemistry , organic chemistry , catalysis , nucleotide , biochemistry , materials science , mathematics , metallurgy , mathematical analysis , gene
Abstract Morpholinium [ 13 C]formate is obtained by neutralizing an aqueous solution of equivalent amounts of sodium [ 13 C]formate and hydrochloric acid with morpholine. Morpholinium [ 13 C]formate is isolated in crystalline form and characterized. Treatment of 6‐hydroxy‐2,4,5‐triaminopyrimidine sulfate with morpholinium [ 13 C]formate at 200° affords [8‐ 13 C]guanine in 80% yield. There is no necessity to synthesize and isolate [ 13 C]‐N‐formylmorpholine and the intermediate N 5 ‐[ 13 C]formyl pyrimidine derivative. Mass spectrometric analysis shows that the molar isotopic concentration of 13 C label in guanine is identical to that of the morpholinium [ 13 C]formate and there is no isotopic scrambling. The same procedure when used with 4,5,6‐triaminopyrimidine sulfate affords adenine in 85% yield.