Reaktion #47746

Reaktionsgleichung

ethyl acetate

triethylamine

phenylacetylene

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

→

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

Ausbeute 92.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle