227078-96-8

Basic information

• Product Name: ETHYL 4-BUTYL-6-METHYL-2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 4-BUTYL-6-METHYL-2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE
• CAS NO: 227078-96-8
• Molecular Formula: C12H20N2O3
• Molecular Weight: 0
• Mol File: 227078-96-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 4-BUTYL-6-METHYL-2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-BUTYL-6-METHYL-2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE(227078-96-8)
• EPA Substance Registry System: ETHYL 4-BUTYL-6-METHYL-2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE(227078-96-8)

Safety Data

• Hazardous Substances Data: 227078-96-8(Hazardous Substances Data)

Upstream product

• 110-62-3 pentanal 
• 141-97-9 ethyl acetoacetate 
• 57-13-6 urea 
• 71-41-0 pentan-1-ol 
• 109-65-9 1-bromo-butane 
• 6214-64-8 6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester 

Relevant articles and documents

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.

Dihydropyrimidinones: Efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity

A simple, efficient, cost-effective, recyclable and green approach has been developed for the synthesis of new dihydropyrimidinone analogs via the Biginelli reaction. The methodology involves a multicomponent reaction catalyzed by "HPA-Montmorillonite-KSF"as a reusable and heterogeneous catalyst. This method gives an efficient and much improved modification of the original Biginelli reaction, in terms of yield and short reaction times under solvent free conditions. All the derivatives were subjected to cytotoxicity screening against a panel of four different human cancer cell lines viz. colon (Colo-205), prostate (PC-3), leukemia (THP-1) and lung (A549) to check their effect on percentage growth. MTT [3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide] cytotoxicity assay was employed to check IC50 values. Of the synthesized analogs, 16a showed the best activity with IC50 of 7.1 ± 0.8, 13.1 ± 1.4, 13.8 ± 0.9 and 14.7 ± 1.1 μM against lung (A549), leukemia (THP-1), prostate (PC-3) and colon (Colo-205) cancer lines, respectively. The 16a analog was further checked for its effect on cancer cell properties through clonogenic (colony formation) and scratch motility (wound healing) assays and thereby was found that it reduced both the colony formation and migratory properties of the lung cancer cell line (A549). Further, molecular docking studies were performed with 16a to show its binding mode. This journal is

Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction

A well-known Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was performed in an environmentally responsible manner. Large numbers of substrates were screened, and found to give excellent yields of the desired products. In

One pot synthesis of micromolar BACE-1 inhibitors based on the Dihydropyrimidinone scaffold and their Thia and Imino analogues

A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginell

(C5H6N4O)(C5H5N4O)3(C5H4N4O)[Bi2Cl11]Cl2 as a simple and efficient catalyst in Biginelli reaction

A highly efficient and facile procedure for the one-pot three-component synthesis of 3,4-dihydropyrimidin-2-(1H)ones/thiones from the one-pot condensation of aldehyde, β-dicarbonyl compound and urea/thiourea was developed. The methodology is applicable to

Nanoparticles of organosilane-based NaHSO4 ionic liquid immobilized on silica as reusable heterogeneous catalyst for one-pot synthesis of 2-oxo-and thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidines

Background: In spite of the fact that there are numerous reagents and methods to synthesize the dihydropyrimidinones via Biginelli reaction, but excellent yields, shorter reaction time and easy work-up are important factors which are not usually found tog

Polymer-supported benzimidazolium based ionic liquid: An efficient and reusable Br?nsted acid catalyst for Biginelli reaction

A polymer-supported benzimidazolium based ionic liquid (PSBIL) was synthesized by reaction of poly(vinylbenzyl chloride) and benzimidazole followed by ring opening of 1,4-butane sultone and acidification with sulphuric acid. The resulting Br?nsted acid he

Phytic acid: A biogenic organocatalyst for one-pot Biginelli reactions to 3,4-dihydropyrimidin-2(1H)-ones/thiones

The natural organocatalyst phytic acid catalyzed one-pot Biginelli reactions by coupling β-ketoesters, aldehydes, and (thio)ureas to afford 3,4-dihydropyrimidin-2(1H)-ones/thiones. This phytic acid catalysis featured good to excellent isolated yields, sol

Synthesis of 3,4-dihydropyrimidinones via phase transfer catalysis

3,4-Dihydropyrimidinone and derivatives were synthesized by the one-pot, three-component Biginelli condensation of an aldehyde, β-dicarbonyl compound and urea. Synthesis was carried out in aqueous sodium hydroxide using Aliquat-336 as a phase transfer agent. Compared to the classical Biginelli reaction conditions, this new method cousistently has the advantage of excellent yields and short reaction time.

A simple and efficient one-pot synthesis of 4-alkyl-3,4-dihydropyrimidin- 2(1H)-ones

4-Alkyl-3,4-dihydropyrimidin-2(1H)-ones possess a number of important properties in comparison with their 4-aryl analogues. We show that these compounds can be synthesised by a simple one-pot reaction of urea or thiourea, different aliphatic aldehydes (from acetaldehyde to valeraldehyde) and various dicarbonyl compounds (ethyl acetoacetate, pentane-2,4-dione, N-(4-chlorophenyl)-3-oxobutanamide, acetoacetaldehyde dimethylacetal) in refluxing DMF or HOAc without use of any catalyst. The methylation of 4-alkyl-5-C(O)R-3,4-dihydropyrimidin-2(1H)-ones leads to 1-methyl derivatives.