反应 #6761

反应方程式

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

cyclopentylamine

→

N6-cyclopentyl-5′-O-methyladenosine

反应条件

后处理

1. 1
   其他The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)
2. 2
   其他The product was re-crystallized from CH3CN)

实验过程

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 589 mg, 1.53 mmol) and cyclopentylamine (2.3 mmol, 227 μl). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 476 mg (1.36 mmol, 89%), mp 164–166° C.; Rf 0.51 (eluens 10% MeOH in CH2Cl2). The product was re-crystallized from CH3CN); 1H NMR (DMSO-d6) δ 8.28 (s, 1H, H-8), 8.18 (s, 1H, H-2), 7.70 (d, 1H, J=7.55 Hz, NH), 5.89 (d, 1H, J=4.80 Hz, H-1′), 5.50 (d, 1H, J=5.15 Hz, OH-2′), 5.26 (d, 1H, J=5.15 Hz, OH-3′), 4.56 (q, 1H, J=4.12 Hz, H-2′), 4.13 (q, 1H, J=4.46 Hz, H-3′), 3.99 (q, 1H, J=4.12 Hz, H-4′), 3.57–3.42 (m, 2H, H-5′), 3.28 (s, 3H, OCH 3), 2.01–1.83 (m, 2H, cyclopentyl), 1.73–1.52 (m, 4H, cyclopentyl); MS m/z 350 (M+H)+; Anal. (C16H23N5O4.0.7 CH3CN) C, H, N.

来源