Реакция #461061

Уравнение реакции

4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-2,5-diformamidopyrimidine

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title compound

Выход 71.1%

6-Chloro-9-[4-(diethoxyphosphoryl)butoxy]-2-formamidopurine

Выход 71.1%

Растворители

diethoxymethyl acetate

Условия реакции

Обработка

1. 1
   Температураto cool
2. 2
   Другоеevaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue was dissolved in methanol
4. 4
   workup.STIRRINGconc. aq. NH3 solution (9:1, 5 ml) and stirred at 23° C. for 5 min
5. 5
   ДругоеThe solvents were evaporated under vacuum
6. 6
   Другоеthe product was purified by column chromatography on silica gel (eluted with chloroform: ethanol, 96:4)

Методика

4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-2,5-diformamidopyrimidine (0.330 g, 0.78 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 evaporated to dryness. The residue was dissolved in methanol: conc. aq. NH3 solution (9:1, 5 ml) and stirred at 23° C. for 5 min. The solvents were evaporated under vacuum and the product was purified by column chromatography on silica gel (eluted with chloroform: ethanol, 96:4) to yield the title compound (0.225 g, 71%), m.p. 98° C. (acetonitrile). 1H NMR: δH ((CD3)2SO) 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.76 (6H, m, CH2CH2CH2P), 3.98 (4H, m, (OCH2CH3)2), 4.43 (2H, t, J=6Hz, NOCH2), 8.8 (1H, s, H-8) 9.36 (1H, br.s, NHCHO), 11.29 (1H, br.s, D2O exchangeable, NHCHO).

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