An improved synthesis of 14C-labelled 2,2′-anhydrouridine, 2′-deoxyuridine and 5-ethyl-2′-deoxyuridine

Add time:07/30/2019    Source:sciencedirect.com

The reaction of [14C]CO2, generated from [14C]BaCO3, with ethynylmagnesium bromide (5) at −78°C afforded [14C]propiolic acid (6). Methylation of [14C]propiolic acid and condensation of the resulting [14C]methyl propiolate (7) with the oxazoline (3) afforded [4-14C]2,2′-anhydrouridine (8) in 27.5% radiochemical yield from [14C]BaCO3 (2.0 GBq/mmol). Treatment of 8 with acetyl bromide followed by reduction with tributyltin hydride and deblocking with ammonia in methanol gave [4-14C]2′-deoxyuridine (11) 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 NaCl, reacted with ethylene in the presence of Li2PdCl4, to afford [4-14C]5-(1-methoxyethyl)- and [4-14C]5-vinyl-2′-deoxyuridine (13 and 14) which were simultaneously hydrogenated to the required [4-14C]5-ethyl-2′-deoxyuridine (15) using hydrogen gas and 10% palladium on charcoal as catalyst. The radiochemical yield of (15) was 61.5% from [4-14C]2′-deoxyuridine (11) and 15% overall from [14C]BaCO3. The product had a specific activity of 2.0 GBq/mmol.

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