Réaction #6339

Équation de réaction

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

→

title compound

Rendement 94.0%

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

Rendement 94.0%

Solvants

diethoxymethyl acetate

Conditions de réaction

Traitement

1. 1
   Autrethe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (15 ml)
3. 3
   Autrethe reaction mixture was evaporated to dryness
4. 4
   Autrethe residue chromatographed on silica gel (eluted with dichloromethane: methanol, 98:2)

Mode opératoire

A solution of 4-chloro-6-[2-(diethoxyphosphorylmethoxy)ethoxyamino]-5-formamidopyrimidine (2.4 g, 6.3 mmol) in diethoxymethyl acetate (10 ml) was heated at 120° C. for 45 minutes. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was dissolved in methanol (15 ml) and 0.880 ammonia (1 ml). After 15 minutes, the reaction mixture was evaporated to dryness and the residue chromatographed on silica gel (eluted with dichloromethane: methanol, 98:2) to give the title compound as an oil (2.15 g, 94%). IR: νmax (film) 3100, 3070, 2995, 1600, 1570, 1440, 1395, 1335, 1250, 1220, 1170, 1030, 930, 640 cm-1. 1H NMR: δH [(CD3)2SO] 1.23 (6H,t,J=7Hz, (OCH2CH3)2), 3.88 (2H, d, J=8Hz, OCH2P), 3.89 (2H,m, CH2OCH2P), 4.0-4.1 (4H,m, (OCH2CH3)2), 4.61 (2H,m, N--OCH2), 8.82 (1H,s,H-8), 8.97 (1H,s,H-2). Found: C,38.38; H,5.10; N,15.14%. C12H18N4O5PCl. 0.5H2O requires: C,38.56; H,5.12; N,14.99%. Found: m/z 364.0703. C12H18N4O5PCl requires: m/z 364.0701.

Source