5'-Chloro-5'-deoxy-8-phenyladenosine → 5'-Deoxy-5'-methylamino-8-phenyladenosine

Participants

Reaction Steps

Compound 4d was prepared by the same procedure as described for the preparation of 4a using 3d (2.00 g, 5.52 mmol) and 33% methylamine/ethanol solution (40 mL). After column chromatography (elution with 4:1:0.2 chloroform:methanol:NH4OH), a yellow glassy solid was obtained: 963 mg (49%); MS m/z 357 (M+H)+; 1HNMR (DMSO-d6) δ 8.19 (s, 1H, H-2), 7.72-7.76 (m, 2H, 8-phenyl o-H's), 7.58-7.61 (m, 3H, 8-phenyl m- and p-H's), 7.40 (bs, 2H, 6-NH2), 5.70 (d, 1H, H-1′, J1′,2′=6.4 Hz), 5.38 (d, 1H, 2′-OH, J2′-2′OH=6.2 Hz), 5.29 (ddd, 1H, H-2′, J1′,2′=6.4 Hz, J2′,3′=5.1 Hz, J2′-2′OH=6.2 Hz), 5.14 (bs, 1H, 3′-OH), 4.19 (bs, 1H, H-3′), 3.95-4.0 (m, 1H, H-4′), 2.82 (d, 2H, 5′-CH2, J=5.2 Hz), 2.34 (s, 3H, 5′NH—CH3).

Provenance & Evidence