Acetic Anhydride → HCID 136153480, compound

Participants

Reaction Steps

(1R,4S)-9-(4-Hydroxymethyl-2-cyclopentenyl)guanine (150 mg, 0.607 mmole), acetic anhydride (freshly distilled, 65 mg, 0.161 mmole), 4-dimethylaminopyridine (3 mg), and dry dimethylformamide (5 mL) were stirred under nitrogen for days. The solvent was evaporated and the residue applied to a silica gel column. Title compound was eluted with 10% methanol-chloroform as a waxy white solid. Crystallization from ethanol gave white powder (123 mg, 70%), m.p. 247°-249° C.; 1H-NMR (DMSO-d6) 10.55 (hr s, 1, NHCO), 7.55 (s, 1, purine H-8), 6.42 (br s, 2, NH2), 6.06 and 5.94 (both m, 2, CH=CH), 5.34 (m, 1, CH--N), 4.07 (d, J=6.0, 2, CH2O), 3.05 (m, 1, CH), 2.6 and 1.55 (both m, 2, CH2), 1.98 (s, 3, COCH3).

Provenance & Evidence