189374-08-1

Basic information

• Product Name: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,6-dimethyl-2-oxo-4-[2-(2-propenyl)phenyl]-, ethyl ester
• CAS NO: 189374-08-1
• Molecular Formula: C18H22N2O3
• Molecular Weight: 314.384
• Mol File: 189374-08-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,6-dimethyl-2-oxo-4-[2-(2-propenyl)phenyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,6-dimethyl-2-oxo-4-[2-(2-propenyl)phenyl]-, ethyl ester(189374-08-1)
• EPA Substance Registry System: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,6-dimethyl-2-oxo-4-[2-(2-propenyl)phenyl]-, ethyl ester(189374-08-1)

Safety Data

• Hazardous Substances Data: 189374-08-1(Hazardous Substances Data)

Upstream product

• 62708-42-3 o-allylbenzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 598-50-5 N-Methylurea 

Downstream Products

• 189374-18-3 4-(2-Allyl-phenyl)-3-(2-methoxycarbonyl-acetyl)-1,6-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 

Relevant articles and documents

Dipolar cycloaddition reactions of dihydropyrimidine-fused mesomeric betaines. An approach toward conformationally restricted dihydropyrimidine derivatives

The bimolecular and intramolecular cycloaddition potential of various 4-aryldihydropyrimidine-fused mesomeric betaines was investigated. Dihydropyrimidine-fused isothiomunchnones and isomunchnones were found to undergo 1,3-dipolar cycloaddition reactions with electron-deficient dipolarophiles such as DMAD, methyl propiolate, methyl vinyl ketone, or N-methylmaleimide. In contrast, cross-conjugated mesomeric thiazinium betaines underwent 1,4-dipolar cycloaddition reaction with electron-rich dipolarophiles such as ynamines or ketene acetals. In general, these cycloadditions show a high degree of regioselectivity, facial selectivity, and exo/endo diastereoselectivity. Intramolecular variations of the above processes involving o-alkenylaryl-tethered dihydropyrimidine-fused isomunchnones lead to polycyclic dihydropyrimidine analogs that closely mimic the proposed receptor-bound conformation of dihydropyridine calcium channel modulators. These cycloadducts are the result of an endo-addition of the π-bond to the carbonyl ylide dipole embedded in the isomunchnone system. The relative stereochemistry of these cycloadducts was established by single-crystal X-ray analysis.