Reacción #6764

Ecuación de reacción

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

3-iodobenzylamine

HCl

→

N6-(3-iodobenzyl)-2-Chloro-5′-O-methyladenosine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2)
2. 2
   OtroThe product was recrystallised from CH3COCH3

Procedimiento

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (61, 372 mg, 0.89 mmol) and 3-iodobenzylamine.HCl (1.34 mmol, 360 mg). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 383 mg (0.72 mmol, 81%), mp 84–86° C.; Rf 0.59 (10% MeOH in CH2Cl2). The product was recrystallised from CH3COCH3; 1H NMR (DMSO-d6) δ 8.89 (bs, 1H, NH), 8.35 (s, 1H, H-8), 7.73 (s, 1H, CCHCI), 7.60 (d, 1H, J=5.83 Hz, CCHCHCH), 7.33 (d, 1H, J=6.12 Hz, CCHCH), 7.12 (t, 1H, J=7.55 Hz, CCHCH), 5.82 (d, 1H, J=5.15 Hz, H-1′), 5.54 (d, 1H, J=5.84 Hz, OH-2′), 5.30 (d, 1H, J=5.49 Hz, OH-3′), 4.61–4.51 (m, 3H, NHCH2, H-2′), 4.09–4.00 (m, 2H, H-3′,4′), 3.56–3.52 (m, 2H, H-5′), 3.28 (s, 3H, OCH3); MS m/z 532 (M+H)−; Anal. (C18H19ClIN5O4.0.3 CH3COCH3) C, H, N.

Fuente