Reaction #1994270

Reaction equation

5-iodo-2′-deoxyuridine

triethylamine

trifluoro-N-prop-2-ynyl-acetamide

bicarbonate

→

crystals

Yield 71.1%

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

Yield 71.1%

Solvents

DMF

Metanol

Conditions

Workup

1. 1
   workup.ADDITIONwere added to the mixture
2. 2
   workup.STIRRINGstirred for 45 min
3. 3
   FiltrationThe mixture was filtered
4. 4
   Washthe filtrate washed with MeOH
5. 5
   Otherthe solvent was removed under vacuum
6. 6
   OtherThe crude mixture was purified by chromatography on silica (ethyl acetate (EtOAc) to EtOAc:MeOH 95:5)

Procedure

To a solution of 5-iodo-2′-deoxyuridine (1.05 g, 2.96 mmol) and CuI (114 mg, 0.60 mmol) in dry DMF (21 ml) was added triethylamine (0.9 ml). After stirring for 5 min trifluoro-N-prop-2-ynyl-acetamide (1.35 g, 9.0 mmol) and Pd(PPh3)4 (330 mg, 0.29 mmol) were added to the mixture and the reaction was stirred at room temperature in the dark for 16 h. Metanol (MeOH) (40 ml) and bicarbonate dowex added to the reaction mixture and stirred for 45 min. The mixture was filtered and the filtrate washed with MeOH and the solvent was removed under vacuum. The crude mixture was purified by chromatography on silica (ethyl acetate (EtOAc) to EtOAc:MeOH 95:5) to give slightly yellow crystals (794 mg, 71%). 1H NMR (d6 dimethylsulfoxide (DMSO)) δ 2.13-2.17 (m, 2H, H-2′), 3.57-3.65 (m, 2H, H-5′), 3.81-3.84 (m, 1H, H-4′), 4.23-4.27 (m, 3H, H-3′, CH2N), 5.13 (t, J=5.0 Hz, 1H, OH), 5.20 (d, J=4.3 Hz, 1H, OH), 6.13 (t, J=6.7 Hz, 1H, H-1′), 8.23 (s, 1H, H-6), 10.11 (t, J=5.6 Hz, 1H, NH), 11.70 (br s, 1H, NH). Mass (−ve electrospray) calcd for C14H14F3N3O6 377.08. Found 376.

Source