Iodine chloride → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-(1-azido-2-iodoethyl)uracil

Temperature

0 °C

Iodine monochloride (50 mg, 0.3 mmol) was added slowly with stirring during a five minute period to a suspension of sodium azide (72 mg, 1.1 mmol) in dry acetonitrile (10 ml) at ice-bath temperature with stirring. This mixture was stirred for a further 5 min., a solution of 20 (66 mg, 0.275 mmol) in dry acetonitrile (40 ml) was added, the reaction mixture was maintained at 0° C. for 30 min. with stirring. The resulting red-brown colored reaction mixture was poured onto ice cold water (25 ml), the mixture was extracted with ethyl acetate (3×50 ml) and the ethyl acetate extract was washed with 5% aqueous sodium thiosulfate (30 ml). Drying the colorless ethyl acetate fraction. (Na2SO4), removal of the solvent in vacuo and purification of the residue obtained by elution from a silica gel column using chloroform:methanol (90:10, v/v) as eluent afforded 21c (24 mg, 21%) as a viscous oil.

1. stirringThis mixture was stirred for a further 5 min.
2. stirringwith stirring
3. additionThe resulting red-brown colored reaction mixture was poured onto ice cold water (25 ml)
4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
5. extractionthe ethyl acetate extract
6. washwas washed with 5% aqueous sodium thiosulfate (30 ml)
7. dry with materialDrying the colorless ethyl acetate fraction
8. custom(Na2SO4), removal of the solvent
9. customin vacuo and purification of the residue
10. customobtained by elution from a silica gel column

ORD record

ord-468575b97a7245ec9d3b434003cc29c2

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589077B2