Ammonia → HCID 54313128, compound

Participants

Reaction Steps

2',3'-Di-O-benzoyl-2-chloro-5'-deoxy-5'-methylene-N-(4-phenylthio-1-piperidinyl)adenosine, prepared as described in Example 25 from 2,6-dichloro-9-(5'-deoxy-2',3'-di-O-benzoyl-5'-methylene-β-D-ribofuranosyl)-9H-purine (1.0 g, 1.9 mmol) and 1-amino-4-phenylthiopiperidine (0.44 g, 2.1 mmol), was dissolved in methanol (20 ml) and sat. methanolic ammonia (2.5 ml) was introduced. The reaction mixture was stirred at ambient temperature for 18 h, evaporated and purified by flash chromatography eluting with a mixture of dichloromethane and ethanol (50:1) to provide the title 2-chloro-5'-deoxy-5'-methylene-N-(4-phenylthio-1-piperidinyl)adenosine (0.27 g, 29%) as a foam, 1H-NMR (400 MHz, DMSO-d6) δ1.70 (2H, br q, piperidine C--H), 1.99 (2H, br d, piperidine C--H), 2.77 (2H, br m, piperidine C--H), 3.06 (2H, br m, piperidine C--H), 4.07 (1H, q, H-3'), 4.32 (1H, dt, H-2'), 4.58 (1H, m, H-4'), 5.20 (1H, dd, C=C--H), 5.29 (1H, d, C=C--H), 5.39, 5.56 (2H, 2d, 2'-and 3'-OH), 5.86 (1H, d, H-1'), 6.07 (1H, m, C=C--H), 7.23-7.45 (5H, 3 m, Ar--H), 8.36 (1H, s, H-8), 9.34 (1H, s, N--H). HPLC retention time 13.46 min. (gradient elution over 30 min; 25-45% acetonitrile/0.1% ammonium sulfate in water), purity 100% at 250 nm).

Provenance & Evidence