Ammonia → HCID 44323083, compound

Participants

Reaction Steps

1-Amino-4-phenylthiopiperidine (1.10 g, 6.7 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.5 g, 4 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(4-phenylthio-1-piperidinyl)adenosine (1.25 g, 65%) as a foam, 1H NMR (DMSO-d6) δ3.51-3.60 (1H, m, H-5'a), 3.62-3.68 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.50 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.21, 5.50 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 7.24-7.45 (5H, 2m, Ar-H), 8.41 (1H, s, H-8), 9.44 (1H, s, N-H).

Provenance & Evidence