반응 #6766

반응 방정식

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

3-iodobenzylamine

HCl

→

N6-(3-Iodobenzyl)-5′-O-Ethyladenosine

반응 조건

후처리

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

실험 절차

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (62, 367 mg, 0.92 mmol) and 3-iodobenzylamine.HCl (1.38 mmol, 372 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 339 mg (0.66 mmol, 72%), mp 164–166° C.; Rf 0.40 (10% MeOH in CH2Cl2). The product was re-crystallized from CH3CN; 1H NMR (DMSO-d6) δ 8.45 (bs, 1H, NH), 8.37 (s, 1H, H-8), 8.21 (s, 1H, H-2), 7.71 (s, 1H, CCHCI), 7.57 (d, 1H, J=7.90 Hz, CCHCHCH), 7.34 (d, 1H, J=6.52 Hz, CCHCH), 7.09 (t, 1H, J==6.87 Hz, CCHCH), 5.91 (d, 1H, J=4.46 Hz, H-1′), 5.53 (d, 1H, J=5.49 Hz, OH-2′), 5.27 (d, 1H, J=4.80 Hz, OH-3′), 4.67–4.64 (m, 2H, NHCH2), 4.56 (q, 1H, J=4.81 Hz, H-2′), 4.17 (q, 1H, J=4.81 Hz, H-3′), 4.00 (q, 1H, J=4.12 Hz, H-4′), 3.60 (dq, 2H, J=9.61 Hz, J=3.43 Hz, H-5′), 3.47 (q, 2H, J=6.52 Hz, OCH2CH3), 1.12 (t, 3,3 J=6.52 Hz, CH3); MS m/z 512 (M+H)+; Anal. (C19H22IN5O4.0.3 CH3CN) C, H, N.

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