4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-5-formamidopyrimidine → 6-Chloro-9-[4-(diethoxyphosphoryl)butoxy]purine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-5-formamidopyrimidine (0.470 g, 1.24 mmol) was dissolved in diethoxymethyl acetate (4 ml) and the resulting solution was stirred at 120° C. for 2 hr. The reaction mixture was then allowed to cool and the solution evaporated to dryness. The residue was dissolved in methanol: conc. aq. NH3 solution (9:1, 5 ml) and stirred at 23° C. for 10 min. The solvents were evaporated under vacuum and the product was purified by column chromatography on silica gel (eluted with chloroform: ethanol, 98:2) to yield the title compound (0.360 g, 81%). 1H NMR: δH [(CD3)2SO] 1.34 (6H, t, J=7Hz, (OCH2CH3)2), 1.89 (6H, m, CH2CH2CH2P), 4.12 (4H, m, (OCH2CH3)2), 4.51 (2H, t, J= 6Hz, NOCH2), 8.28 (1H, s), 8.78 (1H, s). m/z (FAB positive ion) 363 (MH+).

Provenance & Evidence