Reacción #6356

Ecuación de reacción

9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine

trimethylsilyl bromide

→

title compound

9-[2-(Phosphonomethoxy)ethoxy]adenine

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue dissolved in methanol (10 ml)
3. 3
   OtroThe solvent was evaporated
4. 4
   workup.DISSOLUTIONthe residue again dissolved in methanol
5. 5
   Otrosolvent evaporated
6. 6
   Otroto give a solid residue
7. 7
   OtroCrystallisation from methanol

Procedimiento

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%.

Fuente