Reacción #6767

Ecuación de reacción

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

cyclopentylamine

→

N6-cyclopentyl-2-Chloro-5′-O-ethyladenosine

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (63, 505 mg, 1.16 mmol) and cyclopentylamine (1.74 mmol, 172 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 323 mg (0.81 mmol, 70%), mp 114–116° C.; Rf 0.55 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.34 (s, 1H, H-8), 8.32 (bs, 1H, NH), 5.82 (d, 1H, J=5.15 Hz, H-1′), 5.53 (d, 1H, J=5.18 Hz, OH-2′), 5.29 (d, 1H, J=5.15 Hz, OH-3′), 4.47–4.37 (m, 2H, CH, H-2′), 4.11–4.10 (m, 1H, H-3′), 4.00 (q, 1H, J=4.47 Hz, H-4′), 3.62–3.58 (m, 2H, H-5′), 3.47 (q, 2H, J=7.21 Hz, CH2CH3), 2.00–1.83 (m, 2H, cyclopentyl), 1.71–1.51 ((m, 4H, cyclopentyl), 1.12 (t, 3H, J=7.21 Hz, CH3); MS m/z 399 (M+H)+; Anal. (C17H24ClN5O4) C, H, N.

Fuente