301359-45-5

Usage

General Description

The chemical "5-PyriMidinecarboxylic acid, 4-(2-chlorophenyl)-1,2,3,4-tetrahydro-6-Methyl-2-thioxo-, ethyl ester" is an organic compound with the molecular formula C16H18ClN3O2S. It is an ethyl ester derivative of a 4-(2-chlorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid. 5-PyriMidinecarboxylic acid,4-(2-chlorophenyl)-1,2,3,4-tetrahydro-6-Methyl-2-thioxo-, ethyl ester has potential applications in the field of pharmaceuticals and agrochemicals due to its structural and chemical properties. It may be used for the synthesis of various pharmaceutical drugs and can also be employed as an intermediate in organic synthesis. Additionally, it possesses certain biological activities that make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 17849-38-6 2-Chlorobenzyl alcohol 
• 1147550-11-5 ammonium thiocyanate 
• 141-97-9 ethyl acetoacetate 
• 89-98-5 2-chloro-benzaldehyde 
• 17356-08-0 thiourea 

Downstream Products

• 1034918-24-5 6-ethoxycarbonyl-7-methyl-5-(2-chlorophenyl)-5H-thiazolo[3,2-a]pyrimidine 
• 1425352-64-2 ethyl 5-(2-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate hydrochloride 
• 313276-45-8 C₁₆H₁₅ClN₂O₃S 
• 455927-22-7 4-(2-chlorophenyl)-6-methyl-N-4-fluoro phenyl-2-thioxo-1,2,3,4-tetrahydro pyrimidine-5-carboxamide 
• 1426661-08-6 C₂₈H₂₆Cl₂N₄O₄S 
• 361481-37-0 C₁₄H₁₄ClN₅O₂ 

Relevant academic research and scientific papers

Synthesis and characterization of sulfonated-phenylacetic acid coated Fe3O4 nanoparticles as a novel acid magnetic catalyst for Biginelli reaction

Abstract In this paper, we wish to report the synthesis and characterization of sulfonated-phenylacetic acid coated on Fe3O 4 nanoparticles by a simple method. This catalyst was effectively employed as a novel acid magnetic catalyst

Synthesis of Novel 3,4-Dihydropyrimidinones on Water Soluble Solid Support Catalyzed by Indium Triflate

Syntheses of several new 3,4-dihydropyrimidinones (DHPMs) on sodium sulfate solid support have been reported. The microwave enhanced rapid synthesis of the title compounds yielded a good percentage of the DHPMs. The catalytic activity of indium triflate e

Synthesis of novel calcium channel blockers with ACE2 inhibition and dual antihypertensive/anti-inflammatory effects: A possible therapeutic tool for COVID-19

Hypertension has been recognized as one of the most frequent comorbidities and risk factors for the seriousness and adverse consequences in COVID-19 patients. 3,4-dihydropyrimidin-2(1H) ones have attracted researchers to be synthesized via Beginilli reaction and evaluate their antihypertensive activities as bioisosteres of nifedipine a well-known calcium channel blocker. In this study, we report synthesis of some bioisosteres of pyrimidines as novel CCBs with potential ACE2 inhibitory effect as antihypertensive agents with protective effect against COVID-19 infection by suppression of ACE2 binding to SARS-CoV-2 Spike RBD. All compounds were evaluated for their antihypertensive and calcium channel blocking activities using nifedipine as a reference standard. Furthermore, they were screened for their ACE2 inhibition potential in addition to their anti‐inflammatory effects on LPS-stimulated THP‐1 cells. Most of the tested compounds exhibited significant antihypertensive activity, where compounds 7a, 8a and 9a exhibited the highest activity compared to nifedipine. Moreover, compounds 4a,b, 5a,b, 7a,b, 8a,c and 9a showed promising ACE2:SARS-CoV-2 Spike RBD inhibitory effect. Finally, compounds 5a, 7b and 9a exerted a promising anti-inflammatory effect by inhibition of CRP and IL-6 production. Ultimately, compound 9a may be a promising antihypertensive candidate with anti-inflammatory and potential efficacy against COVID-19 via ACE2 receptor inhibition.

Synthesis and catalytic application of D-glucose derived ytterbium(III) complex in Biginelli reaction

4,6-O-Ethylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine has been reacted with ytterbium(III) acetate and the resultant complex has been used as catalyst in the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones (DHPMs). Twenty-one DHPMs have been synthesised under neat reaction condition in appreciable yields (73–96percent) and reusability of the catalyst has been established.

T3P-DMSO mediated one-pot tandem approach for the synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones from alcohols

Background: Biginelli reaction is one of the most important multiple-component chemical reactions which creates 3,4-dihydropyrimidin-2(1H)-ones. Even though Biginelli reaction was reported over a century using different substrates, literature lacks the ex

Bis(p-sulfoanilino)triazine-functionalized silica-coated magnetite nanoparticles as an efficient and magnetically reusable nano-catalyst for Biginelli-type reaction

Abstract: The preparation of bis(p-sulfoanilino)triazine-functionalized silica-coated magnetite nanoparticles and their use as a novel magnetically separable nanocatalyst for the synthesis of various Biginelli adducts are presented. The materials were characterized by various microscopic and spectroscopic techniques such as scanning electron microscopy, vibrating sample magnetometer, X-ray powder diffraction, and FT-IR spectroscopy, etc. A series of 3,4-dihydropyrimidinones or thione products were conveniently prepared by this green protocol from the reactions of aromatic aldehydes with the 1,3-dicarbonyl compounds and urea or thiourea using the catalyst under solvent-free conditions. The present method is operationally simple and offers several advantages such as good to excellent yields, short reaction times, the absence of a solvent, and simple work-up. Moreover, the aforementioned nanocatalyst can be easily recovered from the reaction mixture with the assistance of an external magnetic field and reused several times without any loss of its catalytic activity.

A reactant promoted solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-thione analogues using ammonium thiocyanate

This is the first-time ammonium thiocyanate (NH4SCN) has been used as a self-promoting reactant for the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones. This report describes a greener, efficient and economic protocol for one pot three-component synthesis of Biginelli compounds using various aldehydes, β-ketoesters and ammonium thiocyanate. Ammonium thiocyanate being a weak acid, accelerate the rate of reaction to obtain Biginelli compounds in solvent-free condition at 110?°C. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup and ability to tolerate a variety of functional groups. Ammonium thiocyanate is readily available, cheaper, safer and industrial acceptable material which gives economical as well as ecological rewards to the present method.

Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two novel nanostructured catalysts: applications in the synthesis of Biginelli-type, polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives

Abstract: Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two nanostructured novel, green and heterogeneous catalysts were designed, synthesized and fully characterized by FT-IR, energy-dispersive X-ray spectroscopy, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy and thermal gravimetric analysis. Then their catalytic applications were studied in the Biginelli-type reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via one-pot three-component condensation reaction between several aldehydes, ethyl acetoacetate and urea or thiourea. To further study catalytic properties of NMSDSA and NMSMSA, they were used in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives under same reaction conditions. NMSDSA and NMSMSA have advantages such as cost-effectiveness, cleaner reaction profile, benign and heterogeneous characters, reusability of the catalysts and being in agreement with the green chemistry protocols. The described nanostructured catalysts have natural-based acids and potential for industrial production. Graphical Abstract: Synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via Biginelli-type reaction, polyhydroquinolines and 2,3-dihydroquinazolin-4(1H)-ones using NMSDSA and NMSMSA as two novel nanostructured catalysts. [Figure not available: see fulltext.]

Punica granatum peel: an organocatalyst for green and rapid synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones under solvent-free condition

A novel and green approach was adopted for the synthesis of 3,4-dihydropyrimidin-2(1H)-one/thiones derivatives using Punica granatum peel as an inexpensive, efficient and mild catalyst under solvent-free condition. The methodology is characterized by high

1,3,5-Tris(2-hydroxyethyl)isocyanurate functionalized graphene oxide: A novel and efficient nanocatalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1: H)-ones

In this research, the preparation, characterization and catalytic application of a novel 1,3,5-tris(2-hydroxyethyl)isocyanurate functionalized graphene oxide (GO-THEIC) nanomaterial are described. The GO/THEIC nanomaterial was characterized by Fourier tra