Réaction #1994281

Équation de réaction

TBDMSCl

5-iodo-2′-deoxyuridine

imidazole

→

product ( 33 )

Rendement 90.0%

5′-O-(t-Butyldimethylsilyl)-5-iodo-2′-deoxyuridine

Rendement 90.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with sat. aq. NaCl solution
2. 2
   Extractionextracted with EtOAc
3. 3
   SéchageAfter drying (MgSO4)
4. 4
   Autrethe solvent was removed
5. 5
   Autrethe crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7)

Mode opératoire

To a solution of 5-iodo-2′-deoxyuridine (5.0 g, 14 mmol) in 70 ml in dry N,N-dimethylformamide (DMF) was added imidazole (1.09 g, 16 mmol), followed by (2.41 g, 16 mmol) TBDMSCl at 0° C. The mixture was left in the ice bath and stirred overnight. The reaction was quenched with sat. aq. NaCl solution and extracted with EtOAc. After drying (MgSO4), the solvent was removed and the crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7). The product (33) (5.9 g, 90%) was obtained as a colourless solid. 1H NMR (d6 DMSO) δ 0.00 (s, 3H, CH3), 0.79 (s, 9H, tBu), 1.88-1.97 (m, 1H, H-2′), 2.00-2.05 (m, 1H, H-2′), 3.59-3.71 (m, 2H, H-5′), 3.75 (br s, 1H, H-4′), 4.06 (br s, 1H, H-3′), 5.18 (d, J=4.0 Hz, 1H, OH), 5.98 (t, J=5.9 Hz, 1H, H-1′), 7.89 (s, 1H, H-6), 11.62 (s, 1H, NH). Mass (−ve electrospray) calcd for C15H25IN2O5Si 468.06. Found 467.

Source