Реакция #461072

Уравнение реакции

6-[[1-(t-butyldimethylsilyloxymethyl)-3-(diethoxyphosphoryl)propoxy]amino]-4-chloro-5-formamidopyrimidine

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title compound

Выход 56.0%

9-[1-(t-Butyldimethylsilyloxymethyl)-3-(diethoxy-phosphoryl)propoxy]-6-chloropurine

Выход 56.0%

Растворители

diethoxymethyl acetate

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue dissolved in methanol (5 ml)
3. 3
   workup.ADDITION0.880 ammonia (0.1 ml) added
4. 4
   Другоеthe solvent was evaporated
5. 5
   Другоеthe residue chromatographed on silica gel

Методика

A solution of 6-[[1-(t-butyldimethylsilyloxymethyl)-3-(diethoxyphosphoryl)propoxy]amino]-4-chloro-5-formamidopyrimidine (0.5 g) in diethoxymethyl acetate (5 ml) was heated at 110° C. for 2 hours. The solvent was evaporated under reduced pressure, the residue dissolved in methanol (5 ml) and 0.880 ammonia (0.1 ml) added. After 30 minutes at ambient temperature, the solvent was evaporated and the residue chromatographed on silica gel using dichloromethane-methanol (98:2) as eluant. This afforded the title compound (0.27 g, 56%) as a yellow oil. IR: υmax (film) 2940, 2870, 1595, 1565, 1440, 1390, 1340, 1250, 1220, 1060, 1030, 970, 930, 840, 790 cm-1. 1H NMR: δH (CDCl3) 0.0 (6H, s, SiMe2), 0.8 (9H, s, SiBut), 1.25 (6H, t, J=7Hz, (OCH2CH3)2), 1.8-2.4 (4H, m, CH2CH2P) 3.8 (2H, d, J=6Hz, CH2OSi), 4.1 (4H, m, (OCH2CH3)2), 4.6 (1H, m, CHON), 8.35 (1H, s), 8.75 (1H, s). Found: C, 45.97; H, 6.89; N, 10.80%. C19H34N4O5PSiCl requires: C, 46.28; H, 6.95; N, 11.36%.

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