تفاعل #1994270

معادلة التفاعل

5-iodo-2′-deoxyuridine

triethylamine

trifluoro-N-prop-2-ynyl-acetamide

bicarbonate

→

crystals

المردود 71.1%

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

المردود 71.1%

المذيبات

DMF

Metanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر