Sodium Hydroxide → HCID 178476931, compound

Participants

Reaction Steps

Diethyl 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (100 mg, 0.194 mmol) was dissolved in methanol (5 mL) and 1 N aqueous NaOH solution was added. The reaction mixture was heated at reflux and progress was monitored by HPLC. As soon as all the starting material had been consumed, the reaction mixture was acidified with conc. HCL. After heating at reflux for 1 h, the mixture was evaporated to dryness under vacuum. The product was purified by preparative reverse phase HPLC, yielding ethyl hydrogen 3-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate Example (K) (18 mg, 22%) as a white powder. 1H-NMR (DMSO) δ: 10.0 (s, 1H), 7.65-7.42 (m, 5H), 6.51 (br, 2H), 4.90 (s, 2H), 4.25 (t, J=4.5 Hz, 2H), 3.84 (quint, J=7 Hz, 2H), 3.57 (t, J=4.5 Hz, 2H), 3.26 (s, 3H), 1.13 (t, J=7 Hz, 3H). 31P-NMR (DMSO) δ: 13.04. MS: 424 (MH+).

Provenance & Evidence