Reaction #6762

Reaction equation

6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine

3-iodobenzylamine

HCl

→

N6-(3-iodobenzyl)-5′-O-methyladenosine

Conditions

Workup

1. 1
   OtherThe mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)

Procedure

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 363 mg, 0.94 mmol) and 3-iodobenzylamine.HCl (1.41 mmol, 380 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 397 mg (0.80 mmol, 85%), mp 155–157° C.; Rf 0.54 (eluens 10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.40 (bs, 1H, NH), 8.33 (s, 1H, H-8), 8.21 (s, 1H, H-2), 7.70 (s, 1H, CCHCI), 7.57 (d, 1H, J=6.52 Hz, CCHCHCH), 7.34 (d, 1H, J=5.15 Hz, CCHCH), 7.08 (t, 1H, J=8.93 Hz, CCHCH), 5.89 (d, 1H, J=4.12 Hz, H-1′), 5.50–5.47 (m, 1H, OH-2′), 5.27–5.25 (m, 1H, OH-3′), 4.68–4.56 (m, 3H, H-2′, NHCH2), 4.14–4.13 (m, 1H, H-3′), 4.01–3.98 (m, 1H, H-4′), 3.57–3.53 (m, 2H, H-5′), 3.31 (s, 3H, OCH3); MS m/z 498 (M+H)+; Anal. (C18H20N5O4) C, H, N.

Source