Ju Xiu-lia
2015
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Journal
Journal of Wuhan Institute of Technology
Abstract
4-((4-chloropyrimidin-2-yl)amino)benzonitrile(Ⅰ) is an important intermediate of diarylpyrimidine HIV-1 reverse transcriptase inhibitors and its derivatives. 2-(methylthio)pyrimidin- 4(1H)-one(Ⅱ)was prepared at room temperature from 2-thiouracil using iodomethane as methylation reagent and sodium hydroxide as base. The yield of crudeⅡ reached 83.5% under the optimized molar ratio of 1.00(2-thiouracil) :1.25(iodomethane): 1.05(sodium hydroxide).With no further purification, such as recrystallization, Ⅱreacted with para-aminobenzonitrile in the absence of solvent at 180-190℃ and the crude4-((4-oxo-1,4-dihydropyrimidin-2-yl)amino)benzonitrile(Ⅲ) was obtained with a yield of 71.9%. Then, the unpurified Ⅲreacted withphosphorus oxychloride and the chlorinated product was obtainedwith a yield of 67.3%. The threestep total yield of Ⅰreached 40.4%(calculated from 2-thiouracil). The structure of Ⅰwas confirmed byproton nuclear magnetic resonance spectra and carbon-13 nuclear magnetic resonance spectra, which showed no any other chemical shift of impurities except for the characteristic absorption peaks ofⅠ. Now the data of nuclear magnetic resonance have not been reported publicly.