Ammonia → HCID 44323111, compound

Participants

Reaction Steps

The title compound was prepared according to method A as described in Example 6 by reacting 1-amino-4-phenylpiperazine hydrochloride (also prepared using the method described by Overberger, C. G. and Herin, L. P., Journal of Organic Chemistry, 1962, 27, 417) (0.77 g, 3.0 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-piperazinyl)adenosine (0.81 g, 60%) (after column chromatography) as a foam, 1H NMR (DMSO-d6) δ3.53-3.60 (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'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.77-7.26 (5H, 3m, Ar-H), 8.44 (1H, s, H-8), 9.50 (1H, s, N-H).

Provenance & Evidence