Pyridine → 5'-Chloro-5'-deoxy-8-(methylamino)adenosine

Participants

Reaction Steps

Compound 3c was prepared by the same procedure as described for the preparation of 3a using 2c41 (2.9 g, 9.78 mmol), pyridine (1.54 g, 1.57 mL, 19.46 mmol), CH3CN (5 mL), and SOCl2 (5.82 g, 3.56 mL, 48.91 mmol): yield 1.95 g (63%); MS m/z 315 (M+H)+; 1HNMR (DMSO-d6) δ 7.91 (bs, 1H, H-2), 6.78 (q, 1H, 8CH3—NH), 6.50 (bs, 2H, 6-NH2), 5.70 (d, 1H, H-1′, J1′,2′=5.0 Hz), 5.41 (d, 1H, 2′-OH, J2′-2′OH=5.6 Hz), 5.32 (d, 1H, 3′-OH, J3′-3′OH=5.3 Hz), 5.18 (ddd, 1H, H-2′, J1′,2′=5.0 Hz, J2′,3′=5.4 Hz, J2′-2′OH=5.6 Hz), 4.33 (ddd, 1H, H-3′, J2′,3′=5.4 Hz, J3′,4′=4.4 Hz, J3′-3′OH=5.3 Hz), 3.91-4.02 (bm, 2H, H-4′,5′-CH2), 3.76-3.82 (m, 1H, 5′-CH2), 2.88 (d, 3H, 8NH—CH3, J=4.5 Hz).

Provenance & Evidence