Реакция #461065

Уравнение реакции

4-chloro-6-[[3-(diethoxyphosphoryl)-propoxy]amino]-5-formamidopyrimidine

ammonia

→

title compound

Выход 87.3%

6-Chloro-9-[3-(diethoxyphosphoryl)propoxy]purine

Выход 87.3%

Растворители

methanol

diethoxymethyl acetate

Условия реакции

Обработка

1. 1
   Другоеexcess solvent was removed under reduced pressure
2. 2
   Другоеto leave an oil
3. 3
   Другоеthe solvent was evaporated
4. 4
   Другоеto leave an oil
5. 5
   ДругоеPurification by column chromatography on silica gel (dichloromethane:methanol, 96:4 as eluant)

Методика

A solution of 4-chloro-6-[[3-(diethoxyphosphoryl)-propoxy]amino]-5-formamidopyrimidine (0.86 g, 2.3 mmol) in diethoxymethyl acetate (5 ml) was heated at 120° C. for 2 hours. After cooling to ambient temperature, excess solvent was removed under reduced pressure to leave an oil. The oil was dissolved in methanol (20 ml) and 880 ammonia (0.5 ml) was added. After 20 minutes at ambient temperature, the solvent was evaporated to leave an oil. Purification by column chromatography on silica gel (dichloromethane:methanol, 96:4 as eluant) gave the title compound as a yellow oil (0.7 g, 85%). IR: υmax 3065, 3000, 1595, 1560, 1330, 1240, 1215, 1160, 1050, 1025, 960 and 930 cm-1. 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.6-2.1 (4H, m, OCH2CH2CH2P), 4.00 (4H, m, (OCH2CH3)2), 4.50 (2H, t, J=6Hz, OCH2), 8.8 (1H, s), 9.05 (1H, s).

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