2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 22858285, compound

Participants

Reaction Steps

The title compound was prepared according to method A as described in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]benzimidazole hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (1.75 g, 10 mmol) and 2-mercaptobenzimidazole (1.5 g, 10 mmol) followed by acidic hydrolysis] (0.63 g, 2.20 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.0 g, 2.2 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzimidazolyl)thio-2-propyl]-2-chloroadenosine in methanolic ammonia (200 ml) (previously saturated at -10° C.) to provide the title N-[(R)-1-(2-benzimidazolyl)thio-2-propyl]-2-chloroadenosine (0.52 g, 51%) mp 213°-215° C. after column chromatography and trituration with dichloromethane; 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 3.95 (1H, q, H-4), 4.12 (1 H, br q, H-3'), 4.42-4.70 (2H, m, --CHCH3 and H-2'), 5.07 (1H, br, 5'-OH), 5.22, 5.50 (2H, 2 br, 2'- and 3'-OH), 5.82 (1H, d, H-1'), 7.04-7.57 (4H, 2m, Ar-H) 8.42 (1H, s, H-2), 8.73 (1H, d, --NH). HPLC retention time 13.7 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence