反应 #6340

反应方程式

4-chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine

→

title compound

收率 90.0%

6-Chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine

收率 90.0%

溶剂

diethoxymethyl acetate

反应条件

后处理

1. 1
   其他excess solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue dissolved in methanol (20 ml)
3. 3
   其他The solvent was evaporated
4. 4
   其他to leave an oil which
5. 5
   其他was chromatographed on silica gel (eluted with dichloromethane: methanol, 98.2)

实验过程

A solution of 4-chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine (2.8 g, 6.6 mmol) in diethoxymethyl acetate (20 ml) was heated at 120° C. for 2 hours. After cooling to ambient temperature, excess solvent was removed under reduced pressure, the residue dissolved in methanol (20 ml) and 0.880 ammonia (6.5 ml) and the solution stirred at ambient temperature for 1 hour. The solvent was evaporated to leave an oil which was chromatographed on silica gel (eluted with dichloromethane: methanol, 98.2) to give the title compound as a pale yellow oil (2.4 g, 90%). IR: νmax (film) 3480, 3120, 2995, 1710, 1610, 1580, 1510, 1440, 1390, 1330, 1240, 1050, 1030, 970, 920, 780 cm-1 ; 1H NMR δH [(CD3)2SO] 1.23 (6H, t, J=7 Hz, (OCH2CH3)2), 3.87 (2H, d, J=8 Hz, OCH 2P), 3.87 (2H, m, N-OCH2CH2), 4.03 (4H, m, (OCH2CH3)2), 4.56 (2H, m, N-OCH2CH2), 8.75 (1H, s, H-8), 9.38 (1H, br.s, CHO), 11.30 (1H, br.s, D2O exchangeable NHCHO). Found: C, 38.19; H, 4.79; N, 16.74%. C13H19N5O6PCl requires: C, 38.29; H, 4.70; N, 17.17%. Found: m/z 408.0827 (MH+). C13H20N5O6PCl requires: m/z 408.0840 (MH+).

来源