285136-76-7

Upstream product

• 285136-74-5 Isopropyl (4S)-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 
• 331947-79-6 Isopropyl 3-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 285136-73-4 Isopropyl 3-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 99-61-6 3-nitro-benzaldehyde 
• 1161789-88-3 (2S,4S)-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 
• 542-08-5 isopropyl acetoacetate 
• 57-13-6 urea 

Downstream Products

• 112795-97-8 <6S>-1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methylethyl ester 

Relevant academic research and scientific papers

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.

Chemical resolution of inherently racemic dihydropyrimidinones via a site selective functionalization of Biginelli compounds with chiral electrophiles: a case study

Lithiation/substitution of 4-aryl-6-methyl-3,4-dihydropyrimidin-2(1H)-one ester derivatives with n-BuLi can be directed selectively at N-3 or C-6 positions, depending upon nature and equivalents of the base used and 'hardness or softness' of the metalated

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

Synthesis of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H)-ones via enzymatic resolution: preparation of the antihypertensive agent (R)-SQ 32926

A practical and short synthesis of the enantiomerically pure dihydropyrimidone antihypertensive agent (R)-SQ 32926 has been developed. The key step in the synthesis is the enzymatic resolution of an N3-acetoxymethyl-activated dihydropyrimidone precursor b