Cyclopentylamine → N6-cyclopentyl-2-Chloro-5'-O-cyclopropyladenosine

Participants

Reaction Steps

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-β-D-ribofuranosyl)-purine (65, 543 mg, 1.22 mmol) and cyclopentylamine (1.83 mmol, 180 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 400 mg (0.98 mmol, 80%), mp 104–106° C.; Rf 0.51 (10% MeOH in CH2Cl2). The product was re-crystallized from (C2H5)2O; 1H NMR (DMSO-d6) δ 8.34 (bs, 1H, NH), 8.28 (s, 1H, H-8), 5.81 (d, 1H, J=5.15 Hz, H-1′), 5.53 (d, 1H, J=5.84 Hz, OH-2′), 5.29 (d, 1H, J=5.15 Hz, OH-3′), 4.50 (q, 1H, J=5.15 Hz, H-2′), 4.50–4.47 (m, 1H, CH), 4.09–3.99 (m, 2H, H-3′,4′), 3.68–3.63 (m, 2H, H-5′), 1.94–1.89 (m, 2H, cyclopentyl), 1.71-1.50 (m, 4H, cyclopentyl), 0.46–0.41 (m, 4H, OCHCH2CH2); MS m/z 410 (M+H)+; Anal. (C18H24ClN5O4.0.2(C2H5)2O) C, H, N.

Provenance & Evidence