An Efficient One-Pot Synthetic Method for 2,4-Disubstituted 7-Arylpyrido[4,3-d]pyrimidines from 2,4-Disubstituted 6-(Arylethynyl)pyrimidine-5-carbaldehydes and tert-Butylamine

Abstract

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Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines

“…In our previous report 8 we have shown that the cyclization of 2,4-disubstituted 6-arylethynylpyrimidine-5-carbaldehydes 2 with tert-butylamine proceeded via N-(tert-butyl)-N-{4-[(Z)-2-aryl-2-(tert-butylamino)vinyl]pyrimidin-5-yl}methyleneamines 4. The possible mechanism is presented in Scheme 4.…”

“…After heating, the solution was cooled to room temperature, then cold water (10 mL) was added. The precipitate was filtered, dried, and recrystallized to give 5a-t. 8, 14.2, 27.9, 109.3, 115.3, 127.1, 128.8, 129.5, 138.4, 149.6, 157.2, 157.5, 160.8, 171.8 8,66.6,108.9,115.4,127.2,128.9,129.6,138.2,149.5,157.1,157.7,161.9,165.2 ppm. Anal.…”

“…The intermediate compounds were isolated and possible mechanisms of the reactions were discussed. 8 In this paper we wish to report results of our more extensive investigations.…”

“…Compounds 3a,b and 4c-h were prepared according to the method published earlier 6,8. Data for compounds 3a6 and 4e,f 8 have been published in the previous papers.4.3.1.…”