Reacción #6763

Ecuación de reacción

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

cyclopentylamine

→

N6-Cyclopentyl-2-chloro-5′-O-methyladenosine

Condiciones de reacción

Tratamiento posterior

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

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, 505 mg, 1.2 mmol) and cyclopentylamine (1.8 mmol, 178 μL). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 364 mg (0.95 mmol, 79%), mp 124–126° C.; Rf 0.15 (eluens 2% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.33 (bs, 1H, NH), 8.30 (s, 1H, H-8), 5.81 (d, 1H, J=4.46 Hz, H-1′), 5.51 (d, 1H, J=3.36 Hz, OH-2′), 5.29 (d, 1H, J=3.32 Hz, OH-3′), 4.59–4.29 (m, 2H, CH, H-2′), 4.41–3.99 (m, 2H, H-3′,4′), 3.56–3.52 (m, 2H, H-5′), 1.94–1.92 (m, 2H, cyclopentyl), 1.71–1.50 (m, 4H, cyclopentyl); MS m/z 384 (M+H)+; Anal. (C16H22ClN5O4.0.1 CH2Cl2) C, H, N.

Fuente