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Synthesis of 9‐(2‐phosphonylmethoxy)ethyl‐8‐[ 14 C]adenine [ 14 C]PMEA
Author(s) -
Haynes U. J.,
Swigor J. E.,
Bronson J. J.
Publication year - 1992
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.2580311014
Subject(s) - chemistry , hydrolysis , acetonitrile , aqueous solution , dimethylformamide , yield (engineering) , salt (chemistry) , nuclear chemistry , chemical synthesis , methanol , medicinal chemistry , organic chemistry , solvent , in vitro , biochemistry , materials science , metallurgy
The synthesis of [ 14 C] PMEA ( 3 ) was achieved by coupling the sodium salt of 8‐[ 14 C]adenine ( 1 ) with 2‐(diisopropyl‐phosphonymethoxy) ethanol methanesulfonate in N,N‐dimethylformamide at 100°C to provide the diisopropyl ester ( 2 ). Deesterification with bromotrimethylsilane in acetonitrile, followed by concentration and then aqueous hydrolysis of the resulting silylated intermediate produced [ 14 C] PMEA ( 3 ) as a crystalline solid having a radiochemical purity of 99.1% and a specific activity of 88.7 μCi/mg in an overall yield of 30%.