Hydrochloric Acid → N6-(3-Iodobenzyl)-2-chloro-5'-O-cyclopropyladenosine

Participants

Reaction Steps

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-β-D-ribofuranosyl)-purine (65, 483 mg, 1.08 mmol) and 3-iodobenzylamine.HCl (1.63 mmol, 439 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 435 mg (0.78 mmol, 72%), mp 94–96° C.; Rf 0.49 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.93 (t, 1H, J=6.18 Hz, NH), 8.33 (s, 1H, H-8), 7.73 (s, 1H, CCHCI), 7.59 (d, 1H, J=7.90 Hz, CCHCHCH), 7.34 (d, 1H, J=7.55 Hz, CCHCH), 7.11 (t, 1H, J=7.55 Hz, CCHCH), 5.82 (d, 1H, J=5.14 Hz, H-1′), 5.54 (d, 1H, J=5.84 Hz, OH-2′), 5.30 (d, 1H, J=5.15 Hz, OH-3′), 4.61–4.48 (m, 3H, H-2′, NHCH2), 4.09–3.98 (m, 2H, H-3′,4′), 3.68–3.58 (m, 2H, H-5′), 0.45–0.41 (m, 4H, cyclopropyl); MS m/z 559 (M+H)+; Anal. (C20H21ClIN5O4.0.5 H2O) C, H, N.

Provenance & Evidence