Synthesis And Characterization Of 1-(5-(2-(3,3-Dimethyl-1-Butynyl)Pyrimidinyl)-2-Methyl-1-Propanol

Pyrimidine compounds are an important part of nucleic acid in body’s life activities,which participated in metabolic activities of organisms.Under the spotlight,pyrimidine compound was widely applied to the field of agriculture,medicine,etc.The objective of this paper was to synthesize 1-(5(2-(3,3-dimethyl-1-butynyl)pyrimidinyl)-2-methyl-1-propanol and optimize the reaction conditions for each step.We used high performance liquid chromatography(HPLC)to analyze the purity of the product.The products were identified by UV spectroscopy,infraredspectroscopy and nuclear magnetic resonance(NMR)spectroscopy.The whole process of synthesizing1-(5(2-(3,3-dimethyl-1-butynyl)pyrimidinyl)-2-methyl-1-propanol could be divided into five steps.(1)Vinamidinium salt was prepared at 110 °C using bromoacetic acid,N,N-dimethylformamide and phosphorus oxychloride as a starting material in a yield of about 76%.The hydrolysis kinetics of vinamidinium salt was studied by analyzing the violet spectra of vinamidinium salt at different concentrations,solvent and pH.The rate constants of first order reaction were measured;(2)The vinamidinium and thiourea were reacted in aqueous solution to form thiourea compounds,and then the product was refluxed in acetic acid at 110 °C to synthesize 2-mercaptopyrimidine-5-carbaldehyde,the average yield was about 55%;(3)2-mercapto-5-pyrimidine aldehyde and 3,3-dimethyl-1-butyne were used as starting materials to synthesize 2-(3,3-dimethyl-1-alkynyl)-5-pyrimidine aldehyde.In the presence of Pd(OAc)2(PPh3)2 as catalyst,Cu(OAc)2·H2O was used as cocatalyst,and Na2CO3 was the base,and toluene was used as solvent and reacted at 120 °C for three hours.The yield was up to 52.7%;(4)Using iodine and 1,2-dibromoethane as initiator,magnesium and bromoisopropane as raw materials,isopropyl magnesium bromide was synthesized.In anhydrous tetrahydrofuran,the diisopropyl zinc was synthesized by the substitution of isopropyl bromide and zinc chloride.The yield could reach 38.9%.(5)2-(3,3-dimethyl-1-alkynyl)-5-pyrimidine and diisopropyl zinc were subjected to catalytic reaction under low temperature to obtain the desired product1-(5(2-(3,3-dimethyl-1-butynyl)pyrimidinyl)-2-methyl-1-propanol.The product was separated by chiral column.