5'-Chloro-5'-deoxy-8-(methylamino)adenosine → 5'-Deoxy-5',8-bis(methylamino)adenosine

Participants

Reaction Steps

Compound 4c was prepared by the same procedure as described for the preparation of 4a using 3c (1.00 g, 3.17 mmol) and 33% methylamine/ethanol solution (30 mL). After column chromatography (elution with 7:1:0.4 chloroform:methanol:NH4OH), a yellow glassy solid was obtained: 505 mg (51%); MS m/z 310 (M+H)+; 1HNMR (DMSO-d6) δ 7.89 (bs and q, 2H, H-2 and 8CH3—NH), 6.44 (bs, 2H, 6-NH2), 5.84 (d, 1H, H-1′, J1′,2′=7.0 Hz), 5.22 (d, 1H, 2′-OH, J2′-2′OH=6.4 Hz), 5.12 (d, 1H, 3′-OH, J3′-3′OH=4.0 Hz), 4.66 (ddd, 1H, H-2′, J1′,2′=7.0 Hz, J2′,3′=5.4 Hz, J2′-2′OH=6.4 Hz), 4.14 (bm, 1H, H-3′), 3.94-4.0 (bm, 1H, H-4′), 2.90 (d, 3H, 8NH—CH3, J=4.4 Hz), 2.77-2.83 (m, 1H, 5′-CH2), 2.57-2.62 (m, 1H, 5′-CH2), 2.35 (s, 3H, 5′NH—CH3).

Provenance & Evidence