Synthesis of [2-14C]-labelled 2,2′-anhydrouridine and 2'-deoxyuridine derivatives. A convenient route to [2-14C]-labelled 5-ethynyl- and 5-ethyl-2′-deoxyuridine
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Add time:08/05/2019 Source:sciencedirect.com
Reaction of [2-14C]-cyanamide (1) with D(-) arabinose (2) afforded the oxazoline 3. The reaction of 3 with methyl propiolate gave [2-14C]-2,2′-anhydrouridine (4) having a specific activity of 50 mCi (1.9 GBq) mmol−1 in 25% overall radiochemical yield from labelled barium carbonate. Reaction of 4 with acetyl bromide gave 5 which on treatment with tri-n-butyltin hydride gave 6a. Iodination of 6a with iodine monochloride gave the 5-iodo product 6b which on reaction with trimethylsilylacetylene in the presence of a catalytic amount of (Ph3P)2PdCl2 and cuprous iodide gave the 5-trimethylsilylethynyl derivative 6c. Treatment of 6c with sodium methoxide gave 7a which on reduction afforded 7b in 25% overall chemical yield from 2,2′-anhydrouridine.
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