ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Base Information

• Chemical Name: ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
• CAS No.: 123371-45-9
• Molecular Formula: C₁₄H₁₅N₃O₅
• Molecular Weight: 305.29
• Mol file: 123371-45-9.mol

Synonyms:ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Chemical Property of ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

There total 23 articles about ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl acetoacetate (141-97-9) + 4-nitrobenzaldehdye (555-16-8) + urea (57-13-6) → ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (123371-45-9,161374-08-9)

Guidance literature:

With 1-methylimidazole based ionic liquid terminated dendritic moiety prepared from 2,4,6-trichloro-1,3,5-triazine and 1,3-diaminopropane immobilized on 3-aminopropyltriethoxysilane functionalized bentonite; In ethanol; water; at 50 ℃; for 3h; Green chemistry;

DOI:10.1016/j.molliq.2020.114393

Reference yield: 96.0%

monocarbamide dihydrogen sulfate (21351-39-3) + ethyl acetoacetate (141-97-9) + 4-nitrobenzaldehdye (555-16-8) → ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (123371-45-9,161374-08-9)

Guidance literature:

With urea; at 65 ℃; for 3h;

DOI:10.3987/COM-04-10312

Reference yield: 95.0%

ethyl acetoacetate (141-97-9) + 4-nitrobenzyl chloride (100-14-1) + urea (57-13-6) → ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (123371-45-9,161374-08-9)

Guidance literature:

4-nitrobenzyl chloride; With bismuth(III) nitrate; tetrabutyl ammonium fluoride; at 120 ℃;

ethyl acetoacetate; urea; at 120 ℃;

DOI:10.1055/s-2005-861876

upstream raw materials:

ethyl acetoacetate

4-nitrobenzaldehdye

urea

4-nitrobenzyl chloride

Downstream raw materials:

ethyl (R)-6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ethyl (S)-6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

C₁₂H₁₃N₅O₄

ethyl-4-(4-(9-(4-chlorophenyl)-1,2,3,4,5,6,7,8-octahydro-3,3,6,6-tetramethyl-1,8-dioxoacridin-10(9H)-yl)phenyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate

Refernces

• 1、 Gangadasu, Banda,Palaniappan, Srinivasan,Rao, Vaidya Jayathirtha. "One-pot synthesis of dihydropyrimidinones using polyaniline-bismoclite complex. A facile and reusable catalyst for the biginelli reaction". . p. 1285 - 1287. Retrieved 2004.
• 2、 Zhang, Liyuan,Wang, Chuanhu,Zhou, Li,Li, Pinhua,Zhang, Xiuli,Wang, Lei. "Immobilized nickel(II) on organic-inorganic hybrid materials: The effective and reusable catalysts for Biginelli reaction". . p. 74 - 80. Retrieved 2011.
• 3、 Shinde, Bipin,Kamble, Santosh,Gaikwad, Pramod,Ghanwat, Vishvanath,Tanpure, Sagar,Pagare, Pavan,Karale, Bhausaheb,Burungale, Arvind. "Novel catalytic application of Ni@ZnO nanoparticles and ZnO nanoflakes in aqueous solution of NaPTS hydrotrope at room temperature via a green synthesis of 3,4-dihydropyrimidin-2(1H)-ones". . p. 3097 - 3113. Retrieved 2018.
• 4、 Venkatapathy,Magesh,Lavanya,Perumal,Sathishkumar. "A nanocrystalline CdS thin film as a heterogeneous, recyclable catalyst for effective synthesis of dihydropyrimidinones and a new class of carbazolyl dihydropyrimidinones: Via an improved Biginelli protocol". . p. 10989 - 11002. Retrieved 2019.
• 5、 Maiti, Gourhari,Kundu, Pradip,Guin, Chandrani. "One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: An improved procedure for the Biginelli reaction". . p. 2757 - 2758. Retrieved 2003.
• 6、 Rezayati, Sobhan,Kalantari, Fatemeh,Ramazani, Ali,Sajjadifar, Sami,Aghahosseini, Hamideh,Rezaei, Aram. "Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction". supporting information. p. 992 - 1010. Retrieved 2022/01/11.
• 7、 Yao, Bing-Jian,Wu, Wen-Xiu,Ding, Luo-Gang,Dong, Yu-Bin. "Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction". . p. 3024 - 3032. Retrieved 2021/02/05.