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Upstream product

• 219814-75-2 ethyl 4-(4-methoxyphenyl)-1,6-dimethyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 

Downstream Products

• 1391631-74-5 ethyl 4-(4-methoxyphenyl)-1-methyl-2-oxo-6-[(3-cyano-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridin-2-ylthio)-methyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1391631-75-6 ethyl 6-{[3-cyano-4-(2-ethoxyphenyl)-6-oxo-1,4,5,6-tetra-hydropyridin-2-ylthio]methyl}-4-(4-meth-oxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1391631-76-7 ethyl 6-{[3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-ylthio]methyl}-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 924836-38-4 ethyl 6-[(8-bromo-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)methyl]-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 924851-32-1 ethyl 6-[(8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)methyl]-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1414778-34-9 ethyl 6-({[4-(4-chlorophenyl)-3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl]thio}methyl)-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1414778-43-0 ethyl 6-{[(6-tert-butyl-3-cyano-5,6,7,8-tetrahydroquinolin-2-yl)thio]methyl}-4-(4-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1414778-59-8 4-(4-methoxyphenyl)-1-methyl-4,6,8,9,10,11-hexahydropyrimido[4,5:4',5']pyrido[2',3':4,5]thieno[2,3-b]quinoline-2,5(1H,3H)-dione 

Relevant academic research and scientific papers

Reaction of ethyl 4-aryl-6-bromomethyl- 2-oxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylates with n-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

Alkylation of N-methylmorpholinium 4-Ar1-3-cyano-6-oxo-1,4,5,6- tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4- tetrahydropyrimidine-5-carboxylates (10% KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar1-3-cyano-1,4,5,6- tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylates in overall 30-58% yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar1-carbamoyl)-3-cyano-6- methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar1-5-(N-Ar 1-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3, 4-tetrahydropyrimidine-5-carboxylates (37-51%). In the absence of KOH, only the substituted pyridine-2(1H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

The Thorpe-Ziegler-type reaction of 3-cyanopyridine-2(1H)-thiones with Biginelli 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-ones: Cascade assembling of tetra- and pentacyclic heterocyclic scaffolds

3-Cyanopyridine-2(1H)-thiones have been shown to react with Biginelli-type ethyl 4-aryl-6-(bromomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates upon heating in DMF giving rise to ethyl 4-aryl-6-{[(3-cyanopyridin-2-yl)thio] methyl}-2-oxo-1,2,3,4-