Reaktion #6344

Reaktionsgleichung

4,6-dichloro-5-formamidopyrimidine

diethyl [2-acetoxy-1-(aminooxymethyl)ethoxy]methylphosphonate

triethylamine

→

title compound

Ausbeute 60.0%

6-[[3-Acetoxy-2-(diethoxyphosphorylmethoxy)propoxy]amino]-4-chloro-5-formamidopyrimidine

Ausbeute 60.0%

Lösungsmittel

dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe filtrate evaporated
4. 4
   Sonstigeto leave an oil which
5. 5
   Sonstigewas chromatographed on silica gel (eluant dichloromethane:methanol 97:3)

Vorschrift

A mixture of 4,6-dichloro-5-formamidopyrimidine (0.77 g, 4.0 mmol), diethyl [2-acetoxy-1-(aminooxymethyl)ethoxy]methylphosphonate (1.2 g, 4.0 mmol) and triethylamine (0.82 ml, 6 mmol) in dry dioxan (20 ml) was heated at 100° C. for 2 hours. The reaction mixture was cooled, filtered, and the filtrate evaporated to leave an oil which was chromatographed on silica gel (eluant dichloromethane:methanol 97:3) and gave the title compound as a yellow oil (1.08 g, 60%). 1H NMR: δH [(CD3)2SO] 1.23 (6H,t, J=7 Hz, (OCH2CH3)2), 2.03 (3H,s, COCH3), 3.85-4.35 (11H,m, (OCH2CH3)2 +OCH2P+OCH2CHCH2O). m/z: observed 454.1020; C15H24N4O8PCl (M+) requires 454.0996.

Quelle