422
V. Nair et al.
CD3OD) δ 8.24 (s, 1H), 7.39 (d, J = 16Hz, 1H), 7.34 (d, J = 16Hz, 1H),
4.92–4.90 (m, 1H), 4.57–4.54 (m, 1H), 4.11–4.09 (m, 1H), 3.75–3.74 (m,
2H), 2.49–2.46 (m,1H), 2.45 (s, 3H), 2.29–2.27 (m, 1H), 2.05–2.02 (m,
1H); 13C NMR (125MHz, CD3OD) δ 198.1, 157.8, 150.1, 149.1, 141.0, 134.6,
133.4, 124.2, 75.3, 72.3, 63.1, 60.6, 45.4, 29.0, 26.8; UV λmax (MeOH) 233nm
(ε 26100), 337nm (ε 9900); HRMS (ESI) calcd for C15H19N4O5 [M+H]+ for
335.1355, found 335.1345.
2-[(E)-Buta-1,3-dienyl]-9-[(1ꢁR,2ꢁS,3ꢁR,4ꢁR)-2ꢁ,3ꢁ-dihydroxy-
4ꢁ-(hydroxymethyl)cyclo- pentyl] -1H-purin-6(9H)-one (18)
Compound 13 (60 mg, 0.15 mmol) and Pd(PPh3)2Cl2 (8 mg,
0.01 mmol) in anhydrous DMF (5 mL) was treated with (E)-buta-1,3-
dienyltributylstannane (172 mg, 0.50 mmol). This reaction mixture was then
stirred at 95◦C under argon for 24 hours. The solvent was removed under
reduced pressure. The residue was purified by silica gel column chromatog-
raphy to give compound 18 (21 mg, 44.3%):1H NMR (500MHz, CD3OD)
δ 8.15 (s, 1H), 7.64–7.59 (m, 1H), 6.67–6.63 (m, 1H), 6.48–6.45 (m, 1H),
5.73–5.70 (m, 1H), 5.55–5.53 (m, 1H), 4.92–4.88 (m, 1H), 4.58–4.55 (m,
1H), 4.12–4.10 (m, 1H), 3.76–3.75 (m, 2H), 2.49–2.44 (m, 1H), 2.30–2.27
(m, 1H), 2.08–2.05 (m, 1H); 13C NMR (125MHz, CD3OD) δ 158.0, 152.1,
149.6, 140.3, 140.0, 135.4, 123.5, 123.1, 122.9, 75.3, 72.4, 63.1, 60.5, 45.4,
28.9; UV λmax (MeOH) 236 nm (ε 34000), 260 nm (ε 29400), 321 nm (ε
22900); HRMS (ESI) calcd for C15H19N4O4 [M+H]+ for 319.1406, found
319.1404.
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