Ammonia → HCID 44322999, compound

Participants

Reaction Steps

The title compound was prepared according to method A as described above by reacting 1-amino-4-phenylpiperidine (prepared as outlined in Example 6) (0.77 g, 3.6 mmol) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.90 g, 3.0 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(4-phenyl-1-piperidinyl)adenosine (0.49 g, 37%) as a solid which precipitated on evaporation of column chromatography fractions, mp 142°-149° C. 1H NMR (DMSO-d6) δ 3.53-3.60 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.51 (1H, q, H-2'), 5.07 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.18-7.35 (5H, 2m, Ar--H), 8.43 (1H, s, H-8) 9.45 (1H, s, N--H).

Provenance & Evidence