69207-36-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 6-METHYL-2-OXO-4-PHENYL-1,2-DIHYDRO-5-PYRIMIDINECARBOXYLATE is used as a key intermediate in the synthesis of various drugs and pharmacologically active molecules. Its unique structure, including the pyrimidine ring, ethyl ester group, and phenyl group, contributes to its potential biological activities and makes it a valuable component in the development of new therapeutic agents.
Used in Organic Synthesis:
ETHYL 6-METHYL-2-OXO-4-PHENYL-1,2-DIHYDRO-5-PYRIMIDINECARBOXYLATE is used as a versatile building block in organic synthesis. Its ester functionality allows for further chemical modifications, making it a useful precursor for the preparation of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
ETHYL 6-METHYL-2-OXO-4-PHENYL-1,2-DIHYDRO-5-PYRIMIDINECARBOXYLATE is used as a starting material in medicinal chemistry for the design and synthesis of novel drug candidates. Its structural features, such as the pyrimidine ring and phenyl group, can be exploited to modulate the biological activity and pharmacokinetic properties of the resulting compounds, leading to the discovery of new therapeutic agents with improved efficacy and safety profiles.

InChI:InChI=1/C14H14N2O3/c1-3-19-13(17)11-9(2)15-14(18)16-12(11)10-7-5-4-6-8-10/h4-8H,3H2,1-2H3,(H,15,16,18)

Upstream product

• 198826-97-0 ethyl 2-methoxy-4-methyl-6-phenylpyrimidine-5-carboxylate 
• 123237-03-6 ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate 
• 141-97-9 ethyl acetoacetate 
• 100-52-7 benzaldehyde 
• 198826-89-0 ethyl 6-methyl-2-methoxy-4-(phenyl)-1,4-dihydropyrimidine-5-carboxylate 
• 57-13-6 urea 
• 60750-26-7 ethyl 1,2,3,4-tetrahydro-4-methyl-2-oxo-6-phenylpyrimidine-5-carboxylate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 1245716-47-5 ethyl 4-methyl-6-phenyl-2-(tosyloxy)pyrimidine-5-carboxylate 
• 106-48-9 4-chloro-phenol 
• 108-95-2 phenol 

Downstream Products

• 1027326-75-5 C₂₅H₂₂N₄O₄ 
• 1027326-74-4 C₂₄H₂₀N₄O₃ 
• 1027326-76-6 C₂₄H₁₉ClN₄O₃ 
• 1027326-81-3 C₂₁H₁₇ClN₂O₃ 
• 1027326-73-3 ethyl 7-(5-ethoxycarbonyl-2,3-dihydro-2-oxo-6-phenylpyrimidine-4-yl)-1-oxo-3-phenyl-1H-pyrido[1,2-f]pyrimidine-4-carboxylate 
• 1048007-30-2 4-methyl-6-phenyl-2-p-tolyloxy-pyrimidine-5-carboxylic acid ethyl ester 
• 1048007-29-9 4-methyl-6-phenyl-2-p-tolyl-pyrimidine-5-carboxylic acid ethyl ester 
• 928119-10-2 4-methyl-2-phenoxy-6-phenyl-pyrimidine-5-carboxylic acid ethyl ester 
• 80742-17-2 4-methyl-2,6-diphenyl-pyrimidine-5-carboxylic acid ethyl ester 
• 1220560-28-0 2-(p-tolyl)ethynyl-4-methyl-6-phenyl-pyrimidine-5-carboxylic acid ethyl ester 
• 1376766-46-9 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[2-(7-chloroquinolin-4-ylamino)phenylamino]pyrimidine 
• 1376766-47-0 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[4-(7-chloroquinolin-4-ylamino)phenylamino]pyrimidine 
• 1376766-39-0 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[2-(7-chloroquinolin-4-ylamino)ethylamino]pyrimidine 
• 1376766-40-3 5-ethoxycarbonyl-6-methyl-4-phenyl-2-[3-(7-chloroquinolin-4-ylamino)propylamino]pyrimidine 

Relevant academic research and scientific papers

On the reaction of 3,4-dihydropyrimidones with nitric acid. Preparation and X-ray structure analysis of a stable nitrolic acid [1]

A series of substituted 3,4-dihydro-2-pyrimidones (DHPMs) was reacted with nitric acid under different reaction conditions. Treatment of DHPMs with 50-65% nitric acid at 0°C led to the formation of the corresponding dehydrogenated 2-pyrimidones in moderate to good yields. In contrast, reaction of one representative DHPM with 60% nitric acid at 50°C led to an unusually stable nitrolic acid, involving nitration, nitrosation, dehydrogenation step. The molecular structure of this product was determined by X-ray crystallographic analysis.

Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation o

Interrogation of 2,2′-Bipyrimidines as Low-Potential Two-Electron Electrolytes

As utilization of renewable energy sources continues to expand, the need for new grid energy storage technologies such as redox flow batteries (RFBs) will be vital. Ultimately, the energy density of a RFB will be dependent on the redox potentials of the respective electrolytes, their solubility, and the number of electrons stored per molecule. With prior literature reports demonstrating the propensity of nitrogen-containing heterocycles to undergo multielectron reduction at low potentials, we focused on the development of a novel electrolyte scaffold based upon a 2,2′-bipyrimidine skeleton. This scaffold is capable of storing two electrons per molecule while also exhibiting a low (～-2.0 V vs Fc/Fc+) reduction potential. A library of 24 potential bipyrimidine anolytes were synthesized and systematically evaluated to unveil structure-function relationships through computational evaluation. Through analysis of these relationships, it was unveiled that steric interactions disrupting the planarity of the system in the reduced state could be responsible for higher levels of degradation in certain anolytes. The major decomposition pathway was ultimately determined to be protonation of the dianion by solvent, which could be reversed by electrochemical or chemical oxidation. To validate the hypothesis of strain-induced decomposition, two new electrolytes with minimal steric encumbrance were synthesized, evaluated, and found to indeed exhibit higher stability than their sterically hindered counterparts.

Synthesis and Evaluation of Dihydropyrimidinones and Their Derivatives against Meloidogyne incognita

3,4-Dihydropyrimidin-2-ones (DHPMs) were synthesized in good yield using ammonium molybdate as a catalyst under different reaction conditions through ultrasonication technique. Dehydrogenated derivatives of DHPMs, that is, pyrimidin-2-ones were synthesize

Discovery of new phenyl sulfonyl-pyrimidine carboxylate derivatives as the potential multi-target drugs with effective anti-Alzheimer's action: Design, synthesis, crystal structure and in-vitro biological evaluation

Alzheimer's disease (AD) is multifactorial, progressive neurodegeneration with impaired behavioural and cognitive functions. The multitarget-directed ligand (MTDL) strategies are promising paradigm in drug development, potentially leading to new possible therapy options for complex AD. Herein, a series of novel MTDLs phenylsulfonyl-pyrimidine carboxylate (BS-1 to BS-24) derivatives were designed and synthesized for AD treatment. All the synthesized compounds were validated by 1HNMR, 13CNMR, HRMS, and BS-19 were structurally validated by X-Ray single diffraction analysis. To evaluate the plausible binding affinity of designed compounds, molecular docking study was performed, and the result revealed their significant interaction with active sites of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The synthesized compounds displayed moderate to excellent in vitro enzyme inhibitory activity against AChE and BuChE at nanomolar (nM) concentration. Among 24 compounds (BS-1 to BS-24), the optimal compounds (BS-10 and BS-22) displayed potential inhibition against AChE; IC50 = 47.33 ± 0.02 nM and 51.36 ± 0.04 nM and moderate inhibition against BuChE; IC50 = 159.43 ± 0.72 nM and 153.3 ± 0.74 nM respectively. In the enzyme kinetics study, the compound BS-10 displayed non-competitive inhibition of AChE with Ki = 8 nM. Respective compounds BS-10 and BS-22 inhibited AChE-induced Aβ1-42 aggregation in thioflavin T-assay at 10 μM and 20 μM, but BS-10 at 10 μM and 20 μM concentrations are found more potent than BS-22. In addition, the aggregation properties were determined by the dynamic light scattering (DLS) and was found that BS-10 and BS-22 could significantly inhibit self-induced as well as AChE-induced Aβ1-42 aggregation. The effect of compounds (BS-10 and BS-22) on the viability of MC65 neuroblastoma cells and their capability to cross the blood-brain barrier (BBB) in PAMPA-BBB were further studied. Further, in silico approach was applied to analyze physicochemical and pharmacokinetics properties of the designed compounds via the SwissADME and PreADMET server. Hence, the novel phenylsulfonyl-pyrimidine carboxylate derivatives can act as promising leads in the development of AChE inhibitors and Aβ disaggregator for the treatment of AD.

Structure elaboration of isoniazid: synthesis, in silico molecular docking and antimycobacterial activity of isoniazid–pyrimidine conjugates

Abstract: Designing small molecule-based new drug candidates through structure modulation of the existing drugs has drawn considerable attention in view of inevitable emergence of resistance. A new series of isoniazid–pyrimidine conjugates were synthesize

Method for preparing 2-pyrimidinone derivative through oxidative dehydrogenation aromatization

The invention provides a method for preparing a 2-pyrimidinone derivative. The method comprises the following steps of: heating aldehyde, urea, ethyl acetoacetate and a catalyst metal chloride to react to obtain a 3, 4-dihydropyrimidinone derivative, sequ

Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1 H)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines

Chiral phosphoric acid-catalyzed transfer hydrogenation of 2-hydroxypyrimidines has been successfully realized using Hantzsch ester or dihydrophenanthridine as the hydrogen source, furnishing the chiral 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with excelle

Quinolinium Chlorochromate: An Excellent Reagent for N3-C4 Dehydrogenation of Dihydropyrimidinones and their Antifungal Evaluation

To enhance the efficacy of 3,4-dihydropyrimidin-2-ones (DHPMs) as an antifungal agent, their dehydrogenated derivatives, i.e., pyrimidin-2-ones were synthesized employing quinolinium chlorochromate as an oxidizing agent. The synthesized compounds were scr

4-Bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient oxidizing agent for one-pot synthesis of ethyl pyrimidin-2(1H)-one-5-carboxylates

An efficient one-pot synthesis of pyrimidin-2(1H)-ones via three-component condensation of aldehyde, ethyl acetoacetate and urea using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate [BTPBPDS] as an oxidant is described.