Water → HCID 15476591, compound

Participants

Reaction Steps

2-amino-6-chloro-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl) purine (1) [M. J. Robins and B. Uznanski, Can. J. Chem., 59, 2601-2607 (1981)](18.6 mmol, 7.96 g) was dehydrated three times azeotropically with anhydrous pyridine, and dissolved in anhydrous pyridine, then dimethylamine hydrochloride (55.8 mmol, 4.55 g) and diisopropylethylamine (74.4 mmol) were added thereto with stirring at room temperature. The mixture was stirred at room temperature for 15 hours. After confirming completion of the reaction by TLC, water was added to the reaction mixture and concentrated in vacuo. Chloroform was added to the residue, and the organic layer was washed 3 times with water, 2 times with 5% aqueous sodium hydrogen carbonate, once with water and 2 times with 10% aqueous citrate solution, then the organic layer was dried with magnesium sulfate, and dried in vacuo after filtration. The residue was treated with azeotropic distillation with toluene until no odor of pyridine was noted, the product was purified by silica-gel chromatography (dichloromethane-ethanol) to obtain the product (2) 5.42 g (12.4 mmol) (67%). 1H-NMR (500.13 MHz, CDCl3) δ: 7.56 (s, 1H, H8), 6.02 (d, 1H, H1′, J=5.0 Hz), 5.95 (dd, 1H, H2′, J=5.0 Hz), 5.79 (t, 1H, H3′, J=5.0 Hz), 4.69 (s, 2H, 2-NH2), 4.42-4.45 (m, 1H, H4′), 4.34-4.40 (m, 2H, H5′, H5″), 3.43 (br, 6H, N—CH3), 2.13, 2.10, 2.08 (s, 3H, Ac).

Provenance & Evidence