반응 #6340

반응 방정식

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

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title compound

수율 90.0%

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

수율 90.0%

용매

diethoxymethyl acetate

반응 조건

후처리

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

실험 절차

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+).

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