新产品编号:2071347

Chemical Name: 3-(2-Deoxy-beta-D-ribofuranosyl)-6-octylthieno[2,3-d]pyrimidin-2(3H)-one
项目整合开发状态: Biological Testing
项目研究机构: Cardiff University (Originator), CNRS (Originator), Rega Institute for Medical Research (Originator)
合成路线:The known 5-decynyl-2'-deoxyuridine (I) was protected as the bis-silyl ether (II) with chlorotrimethylsilane and triethylamine.Treatment of (II) with POCl3 and triazole produced the triazolyl derivative (III).Finally,reaction of (III) with thioacetic acid gave rise to the desired thienopyrimidine.

合成路线:In another synthetic route,the starting 3',5'-di-O-acetyl-5-iodo-2'-deoxyuridine (IV) was converted to the corresponding 4-thio derivative (V) upon treatment with P2S5.This was S-methylated with iodomethane and triethylamine to give the 4-methylthio pyrimidinone (VI).Palladium-catalyzed coupling of this 5-iodopyrimidine (VI) with 1-decyne (VII) furnished the 5-decynyl nucleoside (VIII).Removal of the methylthio group with NaSH in DMF gave directly the cyclized thienopyrimidine (IX).The remaining acetate esters were finally hydrolyzed by treatment with a methanolic solution of ammonium hydroxide.