GCA-186

2,4(1H,3H)-嘧啶二酮,6-[(3,5-二甲基苯基)甲基]-1-(乙氧基甲基)-5-(1-甲基乙基)-Chemical Name: 6-(3,5-Dimethylbenzyl)-1-(ethoxymethyl)-5-isopropylpyrimidine-1,3-dihydro-2,4-dione; 6-(3,5-Dimethylbenzyl)-1-(ethoxymethyl)-5-isopropyluracil
CAS No. 149950-61-8
项目整合开发状态: Biological Testing
项目研究机构: Kagoshima University (Originator), Showa University (Originator), University of Oxford (Originator)
合成路线:The reaction of the silylated 5-isopropylpyrimidine (I) with chloromethyl ethyl ether (II) by means of KI in dichloromethane gives 1-(ethoxymethyl)-5-isopropyl-2-thiouracil (III),which is condensed with benzaldehyde (IV) by means of lithium diisopropylamide (LDA) in THF,and desulfurized by reaction with H2O2 and NaOH in water to afford 1-(ethoxymethyl)-5-isopropyl-6-(alpha-hydroxybenzyl)uracil (V).The reaction of (V) with acetic anhydride and pyridine gives the acetate (VI),which is finally submitted to hydrogenolysis with H2 over Pd/C in acetic acid/water/dioxane.

合成路线:Lithiation of 1-(ethoxymethyl)-5-isopropyl-2-thiouracil (I) by means of LDA in cold THF,followed by condensation with 3,5-dimethylbenzaldehyde (II) gave the 6-(alpha-hydroxybenzyl) derivative (III).Oxidative hydrolysis of the thione function of (III) with H2O2 afforded the corresponding uracil (IV).Acetylation of (IV) with Ac2O in pyridine provided acetate ester (V),which was subjected to hydrogenolysis in the presence of Pd/C to furnish the title benzyl derivative.