반응 #461062

반응 방정식

4,6-Dichloro-5-formamidopyrimidine

diethyl 4-(aminooxy)butylphosphonate

N,N-diisopropylethylamine

→

title compound

수율 77.2%

4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-5-formamidopyrimidine

수율 77.2%

용매

diglyme

반응 조건

후처리

1. 1
   온도to cool
2. 2
   여과the hydrochloride of N,N-diisopropylethylamine was filtered off
3. 3
   workup.ADDITIONthe filtrate was diluted with chloroform (150 ml)
4. 4
   세척The resulting solution was washed with 4% aq. NaHCO3 (1×20 ml) and water (1×20 ml)
5. 5
   추출The combined aqueous layers were extracted with chloroform (6×20 ml)
6. 6
   농축the combined chloroform solutions were concentrated to an oil
7. 7
   기타The residue was chromatographed on silica gel (eluted with chloroform: ethanol, 96:4)

실험 절차

4,6-Dichloro-5-formamidopyrimidine (0.441 g, 2.3 mmol), diethyl 4-(aminooxy)butylphosphonate (0.4 g, 1.77 mmol) and N,N-diisopropylethylamine (0.8 ml, 4.6 mmol) in diglyme (15 ml) were stirred at 100° C. for 2.5 hr. The reaction mixture was then allowed to cool, the hydrochloride of N,N-diisopropylethylamine was filtered off and the filtrate was diluted with chloroform (150 ml). The resulting solution was washed with 4% aq. NaHCO3 (1×20 ml) and water (1×20 ml). The combined aqueous layers were extracted with chloroform (6×20 ml) and the combined chloroform solutions were concentrated to an oil. The residue was chromatographed on silica gel (eluted with chloroform: ethanol, 96:4) to yield the title compound (0.520 g, 77%). 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.68 (6H, m, CH2CH 2CH2P), 3.9 (2H, m, NOCH2), 3.97 (4H, m, (OCH2CH3)2), 8.14 (1H, s, H-2), 9.5 (1H, br.s, NHOCH2, D2O exchangeable), 11.0 (1H, NHCHO, D2O exchangeable).

출처