285136-78-9

Basic information

• Product Name: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (4R)-
• CAS NO: 285136-78-9
• Molecular Formula: C15H17N3O5
• Molecular Weight: 319.317
• Mol File: 285136-78-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (4R)-(285136-78-9)
• EPA Substance Registry System: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (4R)-(285136-78-9)

Safety Data

• Hazardous Substances Data: 285136-78-9(Hazardous Substances Data)

Upstream product

• 542-08-5 isopropyl acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 57-13-6 urea 
• 1161789-89-4 (2S,4R)-5-isopropoxycarbonyl-6-methyl-3-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one 
• 285136-73-4 Isopropyl 3-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 331947-79-6 Isopropyl 3-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 131275-78-0 Isopropyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 285136-75-6 Isopropyl (4R)-3-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 

Downstream Products

• 112795-98-9 <6R>-1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methyl ester 

Relevant articles and documents

Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.

Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: Asymmetric synthesis of dihydropyrimidines

The highly enantioselective three-component Biginelli condensation catalyzed by a recyclable chiral ytterbium triflate with a novel hexadentate amine phenol ligand containing a pyridyl group has been developed. A wide range of optically active dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with good to excellent enantioselectivities under mild conditions. Copyright

Synthesis and reactions of Biginelli-compounds. Part 23: Chemoenzymatic syntheses of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H)-ones

Enantiomerically pure dihydropyrimidones (DHPMs) were prepared by lipase-catalyzed enzymatic resolution of two types of activated DHPM esters. In the first model series, pivaloyloxymethyl-activated DHPM C5-esters 10a-c were resolved on an analytical scale