新产品编号:2128299

Chemical Name: 5-[3-(2,4-Diaminopyrimidin-5-ylmethyl)-4-methoxyphenoxy]pentanoic acid
项目整合开发状态: Biological Testing
项目研究机构: Harvard Medical School (Originator)
合成路线:Protection of 4-methoxyphenol (I) with methyl chloroformate in the presence of pyridine affords the carbonate ester (II),which is condensed with dichloromethyl methyl ether and TiCl4 to yield alpha-chloro ether (III).Acidic hydrolysis of (III) with HCl furnishes aldehyde (IV),which is converted into the sodium phenoxide (V) by methanolysis of the carbonate ester (IV).Subsequent alkylation of (V) with p-methoxybenzyl bromide (VI) produces the p-methoxybenzyl ether (VII),which is condensed with 3-morpholinopropionitrile (VIII) employing a catalytic amount of NaOMe to give the morpholino acrylonitrile (IX).After conversion of (IX) to the 3-anilino acrylonitrile (X) upon heating with aniline hydrochloride,condensation with guanidine (XI) produces the diaminopyrimidine (XII).The p-methoxybenzyl group of (XII) is then cleaved by treatment with p-toluenesulfonic acid in MeOH,producing phenol (XIII).The sodium salt generated from phenol (XIII) and NaOEt is then alkylated with ethyl 5-bromopentanoate (XIV) to furnish ether (XV).Finally,alkaline hydrolysis of the ethyl ester group of (XV) leads to the title compound.