Acetic Acid → HCID 23541118, compound

Participants

Reaction Steps

4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (12) (0.056 g, 0.13 mmol) was treated with cyclohexene (1 mL), glacial acetic acid 0.5 mL) and 5% palladium on charcoal (0.06 g) in ethanol (5 mL) according to the procedure used for the preparation of compound (4). The crude product was purified by dissolving in water and washing with toluene. The aqueous layer was separated and the solvent removed under vacuum to give the title compound (13) as an amorphous solid (0.034 g, 100%). δH(300 MHz, D2O) 7.64(1H, d, H-6), 6.22(1H, dd, H-1′), 5.72(1H, d, H-5), 4.43(1H, m, H-3′), 3.56(2H, 2d, H-5′), 3.26(1H, d, CH2NH2), 3.05(1H, d, CH2NH2), 2.40(2H, m, H-2′); δC(75.45 MHz, D2O) 166.95, 152.46, 142.67, 103.11, 86.77, 86.43, 73.97, 64.82, 41.59, 39.25; ES +ve m/z 258(M+H)+, 242(M−NH3)+.

Provenance & Evidence