Hydrochloric Acid → HCID 86590000, compound

Participants

Reaction Steps

To a solution of (2-amino-6-iodopurine-9-yl)-acetic acid ethyl ester (13.9 g, 40 mmol) in THF (280 mL) was added triphosgene (5.34 g, 18 mmol) at 0° C. After stirring for additional 5 min, N,N-diisopropylethylamine (24.4 mL) was slowly added and the reaction mixture was stirred for 30 min at 0° C. Then benzhydrol was added and the resulting reaction mixture was allowed to warm to room temperature and stirred for additional 13 h. The reaction mixture was neutralized by addition of 1N HCl solution and saturated with sodium chloride and sodium thiosulfate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with brine (200 mL×2), dried over sodium sulfate, and filtered. The filtrate was evaporated in reduced pressure and the residue was purified by column chromatography to afford the titled compound (15.15g, 68%). 1H-NMR (500 MHz; DMSO-d6) δ 10.88 (bs, 1H), 8.45 (s, 1H), 7.60˜7.20 (m, 10H), 6.79 (s, 1H), 5.08 (s, 2H), 4.15 (q, 2H), 1.17 (t, 3H).

Provenance & Evidence