SR-265579, WIN-65579

1-环戊基-6-(3-乙氧基-4-吡啶基)-3-乙基-4,5-二氢-1H-吡唑并[3,4-d]嘧啶-4-酮Chemical Name: 1-Cyclopentyl-6-(3-ethoxy-4-pyridinyl)-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one
CAS No. 158020-82-7
项目整合开发状态: Preclinical
项目研究机构: Sanofi-Aventis (Originator)
合成路线:Reaction of triethyl orthopropionate (I) with malononitrile (II) at reflux temperature provided (1-ethoxypropylidene)malononitrile (III).Cyclopentanone (IV) was condensed with tert-butyl carbazate (V) to afford the corresponding hydrazone (VI).Subsequent reduction with sodium cyanoborohydride,followed by acid deprotection furnished cyclopentylhydrazine (VII).Then,condensation of (VII) with malononitrile derivative (III) produced pyrazole (VIII).Partial hydrolysis of the cyano group of (VIII) using concentrated sulfuric acid gave carboxamide (IX).

合成路线:Treatment of 4-cyanopyridine N-oxide (X) with phosphorus oxychloride and phosphorus pentachloride under reflux produced a mixture of 2-chloro (XI) and 3-chloropyridines (XII),which were separated by column chromatography.The 3-chloro isomer (XII) was further treated with sodium ethoxide in DMF to produce the ethoxypyridine (XIII).The pyrazolopyrimidine nucleus (XIV) was then obtained by condensation of cyanopyridine (XIII) with aminopyrazole (IX) in the presence of NaH.Finally,diazotization of (XIV) in 50% sulfuric acid converted the aminopyrimidine group into the required pyrimidinone.