Reacción #806268

Ecuación de reacción

2-(6-cyano-1-hexyn-1-yl)adenosine

triethyl phosphate

phosphorous oxychloride

sodium hydroxide

→

triethylammonium 2-(6-cyano-1-hexyn-1-yl)adenosine 5′-monophosphate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Lavadothe resultant mixture was washed with ether
3. 3
   OtroThe aqueous layer was separated
4. 4
   Otrowater was removed under reduced pressure
5. 5
   Otrothe residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40)
6. 6
   ConcentraciónThe thus-obtained fraction was concentrated
7. 7
   Otroto thereby remove the triethylammonium acetate buffer
8. 8
   OtroThe residue was freeze-dried

Procedimiento

Under argon, A 2-(6-cyano-1-hexyn-1-yl)adenosine (2.41 g) was dissolved in triethyl phosphate (15 mL), and, under ice-cooling conditions, phosphorous oxychloride (25.2 mL, 3.9 eq.) was added thereto, followed by stirring at the same temperature for 5 hours. The reaction mixture was added dropwise to a 10% sodium hydroxide solution (300 mL), and the resultant mixture was washed with ether. The aqueous layer was separated and water was removed under reduced pressure, and the residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40). The thus-obtained fraction was concentrated, and the concentrate was subjected to C18 silica gel column chromatography (water:acetonitrile=100:0 to 60:40), to thereby remove the triethylammonium acetate buffer. The residue was freeze-dried, to thereby yield 1.14 g of the above-titled compound as a colorless amorphous substance.

Fuente