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Syntheses of 9-(2′-monoethylphosphonomethoxyethyl)-8-[14C]guanine ([14C]-EPMG) and 9-(2′-phosphonomethoxyethyl)-8-[14C]guanine ([14C]-PMEG)

✍ Scribed by U. J. Haynes; J. E. Swigor

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
201 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of the title compounds [^14^C]‐PMEG (5) and [^14^c]‐EPMG (6) are described. Treatment of [^14^C]guanine with acetic anhydride in 1‐methyl‐2‐pyrrolidinone gave [^14^C]N‐acetylguanine (2). Reaction with 2‐(diethylphosphonomethoxy) ethylmethanesulfonate in N,N‐dimethylformamide in the presence of potassium carbonate yielded 2‐N‐acetyl‐9(2′‐diethylphosphonomethoxyethyl)‐8‐[^14^C]‐guanine (3). Removal of the acetyl group with aqueous methylamine gave 9‐(2′‐ (diethylphosphonomethoxyethyl)‐8‐[^14^C]‐guanine (4). Treatment of the diethylphosphonate ester with sodium hydroxide and acidification with hydrochloric acid gave 9‐(2′‐(monoethylphosphonomethoxyethyl)‐ 8‐[^14^C]‐guanine (5). Silation of the diethylphosphonate ester with bromotrimethylsilane and treatment with water produced 9‐(2′‐phosphonomethyloxethyl)‐8‐[^14^C]guanine (6).

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