HCID 22868433, compound → HCID 53894413, compound

Participants

Reaction Steps

The above 2',3'-di-O-acetyl-2-chloro-5'-deoxy-5'-fluoro-N-(1-piperidinyl)adenosine (0.38 g, 0.8 mmol) was dissolved in methanolic ammonia (15 ml) and stirred for 1 h. The reaction mixture was evaporated in vacuo and the resultant residue was purified by flash chromatography eluting with dichloromethane and 10% ammonia in ethanol (95:5) to afford 2-chloro-5'-deoxy-5'-fluoro-N-(1-piperidinyl)adenosine (1.8 g, 86%) as a white solid, m.p. 199°-201° C. 1H-NMR (400 MHz, DMSO-d6) δ1.35 (2H, br, piperidine C--H), 1.52 (4H, br, piperidine C--H), 2.80 (4H, br, piperidine C--H), 4.10 (1H, ddd, H-4'), 4.20 (1H, br, H-3'), 4.51 (1H, br, H-2'), 4.65 (2H, dd, H-5'a and H-5'b), 5.88 (1H, d, H-1'), 8.28 (1H, s, H-8). HPLC retention time 7.15 min. (gradient elution over 30 min.; 20-80% acetonitrile/0.1% TFA in water). C15H20ClFN6O3, 0.75H2O requires C, 45.2; H, 5.4; N, 21.1. Found: C, 45.2; H, 5.2; N, 20.8%.

Provenance & Evidence