Reacción #1994283

Ecuación de reacción

( 35 )

3′-O-Allyl-5-iodo-2′-deoxyuridine

triethylamine

propargyltrifluoroacetamide

→

crystals

Rendimiento 95.4%

3′-O-Allyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxyuridine

Rendimiento 95.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched
2. 2
   workup.ADDITIONby adding MeOH (10 ml), DCM (10 ml) and bicarbonate dowex
3. 3
   workup.STIRRINGThe mixture was stirred for 30 min
4. 4
   Filtraciónfiltered
5. 5
   OtroThe solvents were removed under vacuum
6. 6
   Otrothe crude product was purified by chromatography on silica (EtOAc: petrol 3:7 to 7:3)

Procedimiento

To a solution of (35) (400 mg, 1.0 mmol) in dry DMF (10 ml) was added CuI (38 mg, 20 μmol) and triethylamine (300 μl, 2.0 mmol). The propargyltrifluoroacetamide (453 mg, 3.0 mmol) was added drop wise, followed by Pd(PPh3)4 (110 mg, 9.5 μmol). The reaction was stirred for 16 h in the dark. The reaction was quenched by adding MeOH (10 ml), DCM (10 ml) and bicarbonate dowex. The mixture was stirred for 30 min and then filtered. The solvents were removed under vacuum and the crude product was purified by chromatography on silica (EtOAc: petrol 3:7 to 7:3). The product was isolated as slightly yellow crystals (398 mg, 95%). 1H NMR (d6 DMSO) δ 2.25-2.43 (m, 2H, H-2′), 3.65-3.76 (m, 2H, H-5′), 4.07-4.17 (m, 3H, H-4′, CH2), 4.21-4.23 (m, 1H, H-3′), 4.34 (d, J=5.5 Hz, 2H, CH2N), 5.25-5.27 (m, 2H, ═CH2, OH), 5.38 (dd, J=1.83, 17.3 Hz, 1H, ═CH2), 5.96-6.06 (m, 1H, ═CH), 6.17 (t, J=6.9 Hz, 1H, H-1′), 8.29 (s, 1H, H-6), 10.17 (t, J=5.5 Hz, 1H, NHTFA), 11.78 (s, 1H, NH). Mass (−ve electrospray) calcd for C17H18F3N3O6 417.11. Found 416.

Fuente