Reacción #1994281

Ecuación de reacción

TBDMSCl

5-iodo-2′-deoxyuridine

imidazole

→

product ( 33 )

Rendimiento 90.0%

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

Rendimiento 90.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente