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Figure 1. The synthesis of protected C5-amino-modified 2'-deoxyuridines from 5-iodo-2'-deoxyuridine. (i) N-propynyltrifluoroacetamide, Pd(PPh3)4, CuI, Et3N, DMF, 60% yield; (ii) N-propenyltrifluoracetamide, Na2PdCl4, aq NaOAc, pH 5.2, 30–50% yield (23); (iii) NiCl2/NaBH4, MeOH, –78°C, 55% yield (for 1–3) (27); (iv) H2, PtO2 in MeOH, 1 h at room temperature, 88% yield.
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