Reaktion #6356

Reaktionsgleichung

9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine

trimethylsilyl bromide

→

title compound

9-[2-(Phosphonomethoxy)ethoxy]adenine

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue dissolved in methanol (10 ml)
3. 3
   SonstigeThe solvent was evaporated
4. 4
   workup.DISSOLUTIONthe residue again dissolved in methanol
5. 5
   Sonstigesolvent evaporated
6. 6
   Sonstigeto give a solid residue
7. 7
   SonstigeCrystallisation from methanol

Vorschrift

To a solution of 9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine (0.63 g, 1.83 mmol) in dry dichloromethane (10 ml) was added trimethylsilyl bromide (1.45 ml, 11 mmol) and the solution stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in methanol (10 ml). The solvent was evaporated and the residue again dissolved in methanol and solvent evaporated to give a solid residue. Crystallisation from methanol: acetone gave the title compound which was recrystallised from methanol: water (0.24 g, 45%), m.p. 241°-244° C. UV: λmax (EtOH) 259 nm (ε 13,500); IR: νmax (KBr) 3428, 3312, 3084, 1685, 1644, 1612, 1484, 1462, 1455, 1336, 1294, 1278, 1255, 1215, 1195, 1104, 1060, 1046, 1033, 955, 934, 892 cm-1. 1H NMR: δH [(CD3)2SO]3.64 (2H,d,J=8.2 Hz, OCH2P), 3.82 (2H,m,N-OCH2CH2O), 4.50 (2H,m, N-OCH2CH2), 7.42 (2H, br.s, D2O exchangeable NH2), 8.15 (1H,s,H-8), 8.38 (1H,s,H-2) 10.0-4.5 (2H,broad, D2O exchangeable PO(OH )2). Found: C,32.84; H,4.41; N: 23.74%. C8H12N5O5P. H2O requires: C,33.01; H,4.19; N:24.06%.

Quelle