반응 #47746

반응 방정식

ethyl acetate

triethylamine

phenylacetylene

3-(β-D-Ribofuranosyl)-5-iodopyridin-2(1H)-one

→

3-(β-D-ribofuranosyl)-5-(2-phenylethynyl)-pyridin-2(1H)-one

수율 92.0%

용매

DMF

반응 조건

후처리

1. 1
   추출the reaction mixture was extracted three times with water (10 ml each)
2. 2
   농축The combined aqueous layers were concentrated under reduced pressure
3. 3
   기타purified by reversed-phase HPLC

실험 절차

3-(β-D-Ribofuranosyl)-5-iodopyridin-2(1H)-one prepared in Example 1(1) (71 mg, 0.20 mmol) was dissolved in DMF (1.0 ml), followed by addition of CuI (6 mg, 0.032 mmol), triethylamine (42 μl, 0.30 mmol), phenylacetylene (33 μl, 0.30 mmol) and Pd(Ph3P)4 (11 mg, 0.010 mol). The reaction mixture was stirred under an argon atmosphere at room temperature for 6 hours. After addition of ethyl acetate (10 ml), the reaction mixture was extracted three times with water (10 ml each). The combined aqueous layers were concentrated under reduced pressure and then purified by reversed-phase HPLC to give 3-(β-D-ribofuranosyl)-5-(2-phenylethynyl)-pyridin-2(1H)-one (60 mg, 92%) as a white product.

출처