新产品编号:2318139

Chemical Name: N-[4-[1(R,S)-(2,4-Diaminofuro[2,3-d]pyrimidin-5-ylmethyl)propyl]benzoyl]-L-glutamic acid
项目整合开发状态: Biological Testing
项目研究机构: Duquesne University (Originator), Roswell Park Cancer Institute (Originator), Tufts University (Originator)
合成路线:Condensation of 2,6-diaminopyrimidin-4-one (I) with 1,3-dichloroacetone (II) affords the furopyrimidine (III).Subsequent reaction of (III) with tributylphosphine provides the phosphonium salt (IV).Treatment of 4-hydroxypropiophenone (V) with trifluoromethanesulfonic anhydride leads to the aryl triflate (VI).This is then subjected to palladium-catalyzed carbonylation under modified Gerlach's conditions to furnish ethyl 4-propionylbenzoate (VII).Wittig condensation between the phosphorane derived from (IV) and keto ester (VII) produces olefin (VIIIa-b) as a mixture of Z/E isomers.Subsequent hydrogenation of (VIIIa-b) over Pd/C gives (IX).The methyl ester group of (IX) is hydrolyzed under alkaline conditions to afford acid (X),which is then activated as the mixed anhydride (XI) with isobutyl chloroformate and triethylamine.

合成路线:Condensation of the mixed anhydride (XI) with diethyl L-glutamate (XII) produces amide (XIII).The ethyl ester groups of (XIII) are finally hydrolyzed by means of NaOH to provide the title compound.