反応 #1994270

反応方程式

5-iodo-2′-deoxyuridine

triethylamine

trifluoro-N-prop-2-ynyl-acetamide

bicarbonate

→

crystals

収率 71.1%

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

収率 71.1%

溶媒

DMF

Metanol

反応条件

後処理

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

実験手順

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.

出典