Sodium Hydroxide → HCID 1284719, compound

Participants

Reaction Steps

Representative procedure for ribose cleavage: 2-{2-[hydroxy-adamantan-2-yl]ethyn-1-yl}adenine. A solution of 2-{2-[hydroxy-adamantan-2-yl]ethyn-1-yl}adenosine (3.486 g, 7.896 mmol) in methanol (100 mL) and 1.0 M HCl (10.0 mL) was stirred at 90° C. in a pressure apparatus for 18–50 h. The pH was adjusted to 4.2 with 5.0 M NaOH and the volume was reduced to half under reduced pressure. After cooling the resulting precipitate was filtered and washed with methanol to afford the pure product as a white solid: yield 2.153 g, 88%. 1H NMR (DMSO-d6) δ 8.13 (s, 1H), 7.25 (br s, 2H), 5.56 (s, 1H), 2.18–2.09, 1.94–1.89, 1.82–1.64, 1.52–1.45 (4×m, 12H). LRMS ESI (M+H+) 310.1.

Provenance & Evidence