An improved synthesis of 14C-labelled 2,2′-anhydrouridine, 2′-deoxyuridine and 5-ethyl-2′-deoxyuridine (original) (raw)
1986, International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes
The reaction of ['+'C]CO,, generated from ["'C]BaC03, with ethynylmagnesium bromide (5) at-78°C afforded ['4C]propiolic acid (6). Methylation of 114Clpropiolic acid and condensation of the resulting ['4C]meth$ iiopiolate (7) with the bxazoline (3) &o;ded [4-'4C]2,2'-anhydrouridine (8) in 27.5% radiochemical vield from I'4C1BaC0, (2.0 GBaimmoll. Treatment of 8 with acetvl bromide followed bv , ~ 1, I , reduction with-tributyltin hydiide and deblocking with ammonia in methanol gave [4-W]2'-deoxyuridine (II) in 88.7% radiochemical yield from 8. The 5-chloromercuri adduct 12, obtained in quantitative yield upon treatment of 11 with mercury(II) acetate and NaCI, reacted with ethylene in the presence of Li,PdCl,, to afford [4-'4C]5-(l-methoxyethyl)-and [4-W]5-vinyl-2'-deoxyuridine (13 and 14) which were simultaneously hydrogenated to the required [4-'4C]5-ethyl-2'-deoxyuridine (15) using hydrogen gas and IO?6 palladium on charcoal as catalyst. The radiochemical yield of (15) was 61.5% from [4-W]2'-deoxyuridine (11) and 15% overall from [W]BaCO,. The product had a specific activity of 2.0 GBq/mmol.
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