5948-71-0

Usage

Uses

Used in Organic Synthesis:
4-(4-Chloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester is used as an organic synthesis intermediate for the preparation of various organic compounds. Its unique molecular structure allows it to serve as a building block in the synthesis of complex molecules, which can be further modified or functionalized to achieve desired properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(4-Chloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester is used as a pharmaceutical intermediate. It plays a crucial role in the development of new drugs, particularly those targeting specific biological pathways or receptors. Its structural diversity and versatility make it a valuable component in the design and synthesis of novel therapeutic agents.
Used in Laboratory Research and Development:
4-(4-Chloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester is also utilized in laboratory research and development processes. It serves as a valuable tool for chemists and researchers to study the properties and reactivity of pyrimidine derivatives, as well as to explore new synthetic routes and methodologies. 4-(4-Chloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester can be used to investigate various aspects of chemical reactions, such as reaction mechanisms, stereochemistry, and selectivity.
Used in Chemical Production Process:
In the chemical production process, 4-(4-Chloro-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester is employed as a key intermediate in the synthesis of various chemicals and materials. Its presence in the production process can lead to the development of new products with improved properties, such as enhanced stability, reactivity, or bioavailability. Additionally, it can contribute to the optimization of existing chemical processes, resulting in more efficient and cost-effective production methods.

Synthesis

Substituted benzaldehyde (6.617×10-3mmol; 1.0 equiv.) is mixed with slightly excess equivalent of urea (6.749×10-3mmol; 1.02 equiv.) and ethyl acetoacetate (6.749×10-3mmol; 1.02 equiv.) in the presence of catalytic concentration 1.0×10-4mmol of our synthesized dimeric pyridinium salts along with dry MeCN at ambient reaction condition from 6-33 min. reaction condition. Yield: 92%

InChI:InChI=1/C14H15ClN2O3/c1-3-20-13(18)11-8(2)16-14(19)17-12(11)9-4-6-10(15)7-5-9/h4-7,12H,3H2,1-2H3,(H2,16,17,19)

Upstream product

• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 141-97-9 ethyl acetoacetate 
• 57-13-6 urea 
• 1522-29-8 (Z)-ethyl 3-hydroxybut-2-enoate 
• 104-88-1 4-chlorobenzaldehyde 
• 55718-52-0 1,1'-((4-chlorophenyl)methylene)diurea 
• 873-76-7 para-Chlorobenzyl alcohol 
• 4254-20-0 4,4'-dichlorobenzoin 
• 37580-81-7 1,2-bis(4-chlorophenyl)-1,2-ethandiol 
• 5315-86-6 4-chlorobenzaldehyde semicarbazone 
• 17356-08-0 thiourea 
• 100-52-7 benzaldehyde 
• 674-82-8 4-methyleneoxetan-2-one 
• 64-17-5 ethanol 

Downstream Products

• 593283-32-0 4-(4-chloro-phenyl)-5-[5-(4-chloro-phenyl)-4H-[1,2,4]triazol-3-yl]-6-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 593283-33-1 4-(4-chloro-phenyl)-5-[5-(4-dimethylamino-phenyl)-4H-[1,2,4]triazol-3-yl]-6-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 593283-31-9 4-(4-chloro-phenyl)-6-methyl-5-[5-(3-nitro-phenyl)-4H-[1,2,4]triazol-3-yl]-3,4-dihydro-1H-pyrimidin-2-one 
• 1012074-52-0 C₁₄H₁₄ClN₃O₄ 
• 302934-30-1 C₁₆H₁₇ClN₂O₄ 
• 1443444-43-6 C₁₄H₁₃Br₂ClN₂O₃ 
• 1443444-51-6 4-(4-chlorophenyl)-4,6-dihydropyrimido[4,5-d]pyridazine-2,5-(1H,3H)-dione 
• 302821-62-1 ethyl 4-(4-chlorophenyl)-1,6-dimethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1394138-72-7 ethyl 4-(4-chlorophenyl)-1-hexadecyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1394138-70-5 ethyl 4-(4-chlorophenyl)-6-methyl-1-octyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1394138-69-2 ethyl 1-butyl-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 

Relevant academic research and scientific papers

Potassium Fluoride-Modified Clay as a Reusable Heterogeneous Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones

Potassium fluoride-modified clay collected from the region of Agadir (Morocco) was used as a hetaerogeneous catalyst in the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-one derivatives via the Biginelli reaction. The products were obtained with excell

Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction

An efficient and heterogeneous novel magnetic silica-coated picolylaminecopper complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)] was synthesized, characterized, and employed as a magnetically recoverable nanocatalyst in Biginelli condensation for the preparatio

Composite of cross-linked chitosan beads and a cyclodextrin nanosponge: A metal-free catalyst for promoting ultrasonic-assisted chemical transformations in aqueous media

A novel carbohydrate-based catalytic composite was prepared through covalent decoration of cross-linked chitosan beads with a cyclodextrin nanosponge. In this regard, chitosan beads were fabricated and cross-linked with glutaraldehyde. Subsequently, they

Fabrication of porous ultrathin carbon nitride nanosheet catalysts with enhanced photocatalytic activity for N- And O-heterocyclic compound synthesis

A simple and efficient photocatalytic method for the synthesis of dihydropyrimidinones (DHPMs) and their derivatives via porous ultrathin carbon nitride nanosheets (p-CNNs) without solvents was demonstrated. The yields of 3,4-dihydropyrimidin-2(1H)-ones/t

Copper-catalyzed one-pot relay synthesis of anthraquinone based pyrimidine derivative as a probe for antioxidant and antidiabetic activity

Synthetic compounds have modernized the globe due to its vast applicable fields. Anthraquinones, as well as pyrimidine derivatives, are used as essential pharmacophores in the field of medicine. Maintenance of a green disease-free environment by using these derivatives is being acknowledged in developed as well as developing countries of the world. Considering the use of active catalysts in the synthesis of anthraquinone based derivatives are the era of concern for researchers due to their distinctive properties. Owing to the remarkable activities of anthraquinone and pyrimidine derivative, we synthesize compounds having both functionalities with the utilization of novel synergically active copper catalysts. This study explores the application of synthesized compounds using fast, ecofriendly and cost-effective approaches.1H and 13C NMR, antioxidant, antidiabetic, molecular docking and QSAR studies were used for characterization and evaluation of newly synthesized anthraquinone based pyrimidine derivatives. The result of these techniques shows that our desired compounds were successfully synthesized and have potent applications. Among all synthesized compounds, G2 and G3 showed a remarkable antioxidant activity with IC50 of 15.09 and 21.88 μg/ml respectively. While the compound G2 and G4 showed a strong inhibitory antidiabetic activity with the IC50 value of 24.23 and 28.94 μg/ml respectively. Furthermore, molecular docking results for both of the proteins assist the experimental data and confirms the different interactions between binding domains and substituent moieties. SAR study also relates to the experimental facts by giving us positive results of synthesized compounds. According to the QSAR study, G4 and G2 emerged as the most stable and most reactive compound among other compounds respectively. While MEP shows moderate to good nucleophilic and electrophilic reactivity of all four compounds.

Porous organic polymer bearing triazine and pyrene moieties as an efficient organocatalyst

Materials with high specific surface area and bearing abundant basic sites at their pore surface are very demanding as heterogeneous catalyst for the eco-friendly base catalyzed reactions. Here we have developed a new secondary amine linked triazine and p

Air-stable zirconium (IV)-salophen perfluorooctanesulfonate as a highly efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under solvent-free conditions

An air-stable complex of zirconium (IV)-salophen perfluorooctanesulfonate (1) was successfully synthesized by reacting Zr (salphen)Cl2 and C8F17SO3Ag. Complex 1 was characterized and studied by different techniq

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethan

Efficient one-pot synthetic methods for the preparation of 3,4-dihydropyrimidinones and 1,4-dihydropyridine derivatives using BNPs?SiO2(CH2)3NHSO3H as a ligand and metal free acidic heterogeneous nano-catalyst

Heterocyclic compounds with biological and pharmacological activates like 3,4-dihydropyrimidin-2-(1H)-ones and 1,4-dihydropyridines have attracted great interest. Boehmite nanoparticles functionalized with silylpropyl sulfamic acid (BNPs?SiO2(C

CoFe2O4?SiO2-NH2-CoII NPs: An effective magnetically recoverable catalyst for Biginelli reaction

Biginelli reaction entails acid-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with simply-accessible initial substances, specifically, aldehyde, urea, and active methylene compound. DHPMs have stimulated a resurgence of attention in the previous two decades because of their broad-ranging pharmacological actions and the existence of varied all-natural products. Currently, green methods to asymmetric Biginelli reaction have been researched for anti-inflammatory DHPMs. In materials chemistry, DHPMs are increasingly decision applications in the creation of materials like polymers, adhesives, fabric dyes, etc. In light of the simplicity by which the Biginelli reaction is conducted, numerous interesting prospects expect its exploitation in variety fields. CoFe2O4?SiO2-NH2-CoII is herein turned out to be an effective catalyst at a three-component Biginelli reaction. The yield of the corresponding DHPMs was rather large (20 cases; average 92 percent). Finally, we herein suggest a procedure that shows lots of advantages and benefits such as the whole lack of solvents, mild reaction conditions, comparatively short reaction times. Also, CoFe2O4?SiO2-NH2-CoII NPs catalyst has been readily recovered from the reaction combination and reused, without the decrease of catalytic action.