Open AccessStudy of lithium aluminium hydride reduction of 5-acetyl-1,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1h)-one
Author(s) -
Blagica Zlatković,
Niko S. Radulović
Publication year - 2017
Publication title -
facta universitatis. series: physics, chemistry and technology
Language(s) - English
Resource type - Journals
eISSN - 2406-0879
pISSN - 0354-4656
DOI - 10.2298/fupct1701017z
Subject(s) - lithium (medication) , yield (engineering) , lithium aluminium hydride , chemistry , methylene , medicinal chemistry , hydride , nuclear chemistry , organic chemistry , materials science , hydrogen , medicine , metallurgy , endocrinology
In this paper, we investigated the LiAlH4-reduction of 5-acetyl-1,6-dimethyl- 4-phenyl-3,4-dihydropyrimidin-2(1H)-one (N-methylated Biginelli compound). Following the reduction and SiO2-promoted dehydration, (Z)-5-ethylidene-1-methyl-6- methylene-4-phenyltetrahydropyrimidin-2(1H)-one was isolated as the major product (33% yield). Chromatographic separation of the reaction products also allowed us to isolate (yield in parentheses) and fully spectrally characterize: 1,6-dimethyl-4-phenyl- 5-vinyl-3,4-dihydropyrimidin-2(1H)-one (20%), 5-ethyl-1,6-dimethyl-4-phenyl-3,4- dihydro-pyrimidin-2(1H)-one (9%), 5-(1-hydroxyethyl)-1,6-dimethyl-4-phenyl-3,4- dihydropyrimidin-2(1H)-one (5%). A possible mechanism explaining the formation of these products is proposed.