Reaktion #1435756

Reaktionsgleichung

SnCl4

5-iodouracil

2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol

NaHCO3

→

title compound 45

Ausbeute 95.0%

1-[[1,3-Bis(benzyloxy)-2-propoxy]methyl]-5-iodouracil

Ausbeute 95.0%

Lösungsmittel

CH2Cl2

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   TemperaturThe resulting clear solution was cooled to 0° C.
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   ExtraktionThe aqueous layer was extracted with CHCl3
5. 5
   Sonstigethe combined organic phase was evaporated
6. 6
   SonstigeThe residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3)

Vorschrift

To a suspension of 2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol (44; prepared according to Martin J. C., Dvorak C. A., Smee D. F., Matthews T. R., Verheyden J. P. H. (1983) 9-[(1,3-Dihydroxy-2-propoxy)methyl]quanine: a new potent and selective antiherpes agent, J. Med. Chem. 26, 759–761) (2.038 g, 5.9 mmol) and 5-iodouracil (2.106 g, 8.85 mmol) in anhydrous CH2Cl2 (25 mL) at room temperature was added N,O-bis-(trimethylsilyl)acetamide (BSA, 5.46 mL, 22.13 mmol), and the mixture was stirred at room temperature under nitrogen for 2 h. The resulting clear solution was cooled to 0° C., and SnCl4 (1 M solution in CH2Cl2, 5.9 mL, 5.9 mmol) was added. The mixture was stirred at room temperature overnight, and then poured into a mixture of saturated aqueous NaHCO3 and CHCl3. The aqueous layer was extracted with CHCl3, and the combined organic phase was evaporated. The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3) to give the title compound 45 as a yellow oil (2.935 g, 95%). 1H NMR (CDCl3) δ 8.59 (s, 1H, NH), 7.82 (s, 1H, H-6), 7.36–7.26 (m, 10H, arom.), 5.28 (s, 2H, CH2N), 4.50 (s, 4H, 2 CH2), 3.99 (m, 1H, CHO), 3.52 (m, 4H, 2 CH2O).

Quelle