53554-29-3

Basic information

• Product Name: 1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER
• Synonyms: 1,4-Dihydro-2-(methylthio)-4-oxo-5-pyrimidine-;1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINECARBOXYLIC ACID ETHYL ESTER >98%;5-PYRIMIDINECARBOXYLICACID,1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-,ETHYLESTER;ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate;Ethyl 1,4-dihydro-2-(methylthio)-4-oxopyrimidine-5-carboxylate;Ethyl 4-hydroxy-2-methylthio-5-pyrimidinecarboxylate;Ethyl 1,4-dihydro-2-(methylsulphanyl)-4-oxopyrimidine-5-carboxylate, 1,4-Dihydro-5-(ethoxycarbonyl)-2-(methylthio)-4-oxopyrimidine;Ethyl 1,4-dihydro-2-(Methylthio)-4-oxo-5-pyriMidinecarboxylate
• CAS NO: 53554-29-3
• Molecular Formula: C₈H₁₀N₂O₃S
• Molecular Weight: 214.24
• Product Categories: pyrimidine
• Mol File: 53554-29-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 136-144°C
• Boiling Point: 340.4 °C at 760 mmHg
• Flash Point: 159.7 °C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 4.37E-05mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• PKA: 6.48±0.50(Predicted)
• CAS DataBase Reference: 1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER(53554-29-3)
• EPA Substance Registry System: 1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER(53554-29-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 53554-29-3(Hazardous Substances Data)

Usage

Uses

1,4-Dihydro-2-methylmercapto-4-oxo-5-pyrimidinecarboxylic acid ethyl ester can be used as several synthetic intermediates and pharmaceutical intermediates, mainly used in laboratory research and development process and pharmaceutical and chemical production process.

Synthesis

Methylthiourea sulfate (75.2g, 0.4mol) was added to 16% NaOH (250mL, 1.18mol) solution and stirred for 30min, then diethyl ethoxymethylenemalonate (103.4g, 0.48 mol) was dissolved in 160 mL of ethanol and slowly dropped into the reaction solution. After the dropwise addition was completed, the reaction was carried out at room temperature for 10 h.When a large amount of white solid was precipitated, carry out suction filtration, wash with water, and vacuum dry to obtain a white solid (84.7g, 99.7%); ESE-MS (m/z): 249[M+H]+, 236.9[M+Na]+ , after verification, the product is 1,4-dihydro-2-methylmercapto-4-oxo-5-pyrimidinecarboxylic acid ethyl ester.

InChI:InChI=1/C8H10N2O3S/c1-3-13-7(12)5-4-9-8(14-2)10-6(5)11/h4H,3H2,1-2H3,(H,9,10,11)

Upstream product

• 38026-46-9 ethyl 4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxilate 
• 77-78-1 dimethyl sulfate 
• 2986-19-8 carbamimidothioic acid methyl ester 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 36239-09-5 ethyl chlorocarbonylacetate 
• 14527-26-5 2-methylisothiourea sulphate 
• 867-44-7 S-Methylisothiourea sulfate 
• 37555-99-0 diethyl ethoxymalonate 
• 147895-43-0 S-methylisothiourea hemisulphate 
• 867-44-7 methyl carbamimidothioate bis(sulfate) 
• 53114-57-1 S-methylisothiourea hydrochloride 

Downstream Products

• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 98771-90-5 ethyl 1,6-dihydro-2-(2-fluoroanilino)-6-oxo-5-pyrimidinecarboxylate 
• 98771-73-4 2-(4-Butoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-68-7 6-Oxo-2-(3-propoxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-71-2 6-Oxo-2-(4-propoxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-80-3 2-(2,5-Dibutoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-85-8 2-(3,4-Dibutoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-56-3 ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate 
• 98771-58-5 ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate 
• 98771-69-8 2-(3-Butoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-63-2 6-Oxo-2-(2-pentyloxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-65-4 2-(2-Hexyloxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98771-79-0 2-(2,5-Dipropoxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 124769-43-3 2-(4-Hydroxy-phenylamino)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 

Relevant articles and documents

Antibacterial activity of 2-amino-4-hydroxypyrimidine-5-carboxylates and binding to Burkholderia pseudomallei 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase

Enzymes in the methylerythritol phosphate pathway make attractive targets for antibacterial activity due to their importance in isoprenoid biosynthesis and the absence of the pathway in mammals. The fifth enzyme in the pathway, 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase (IspF), contains a catalytically important zinc ion in the active site. A series of de novo designed compounds containing a zinc binding group was synthesized and evaluated for antibacterial activity and interaction with IspF from Burkholderia pseudomallei, the causative agent of Whitmore's disease. The series demonstrated antibacterial activity as well as protein stabilization in fluorescence-based thermal shift assays. Finally, the binding of one compound to Burkholderia pseudomallei IspF was evaluated through group epitope mapping by saturation transfer difference NMR.

Method for synthesizing high-purity 4-chloro-2-methylthiopyrimidine-5-ethyl carboxylate

The invention discloses a method for synthesizing high-purity 4-chloro-2-methylthiopyrimidine-5-ethyl carboxylate. The method comprises the following steps: reacting S-methylisothiourea sulfate and diethyl ethoxy-methylene malonate in an ethanol-sodium hydroxide solution, concentrating to remove ethanol and regulating the pH to be acidic to obtain an intermediate, namely 4-hydroxy-2-hydroxyhydroxypyrimidine-5-carboxylic acid ethyl ester, wherein the molar ratio of the S-methylisothiourea sulfate to the diethyl ethoxy-methylene malonate is 1 to 1.9-2.4; enabling the obtained 4-hydroxy-2-hydroxyhydroxy pyrimidine-5-carboxylic acid ethyl ester to react with thionyl chloride to obtain a target product, wherein the molar ratio of the 4-hydroxy-2-hydroxyhydroxy pyrimidine-5-carboxylic acid ethyl ester to the thionyl chloride is 1 to 1-1.8. The improved method provided by the invention can improve the yield, increase the reaction safety and reduce the cost.

Design, synthesis, and biological evaluation of novel catecholopyrimidine based PDE4 inhibitor for the treatment of atopic dermatitis

Selective inhibition of phosphodiesterase (PDE) 4B favorably suppresses the synthesis of inflammatory cytokines and subsequently arrest the development of atopic dermatitis via modulating the intracellular cAMP levels. Considering the side effects of corticosteroids, selective PDE4 inhibition could constitute an effective alternative therapy for the treatment of atopic dermatitis (AD). In this study, a series of novel catechol based compounds bearing pyrimidine as the core have been synthesized and screened for the PDE4 inhibitory properties. The PDE4 selectivity of the active compounds over other PDEs has been investigated. Compound 23 bearing pyrimidine core functionalized with catechol, pyridine and trifluoromethyl groups can effectively inhibit the PDE4B with IC50 value in nanomolar range (IC50 = 15 ± 0.4 nM). Compound 23 exhibited seven fold higher selectivity towards PDE4B over PDE4D. Molecular Docking study confirmed its stronger affinity towards catalytic domain of PDE4B. In-vivo analysis confirmed that compound 23 effectively alleviated the symptoms of atopic dermatitis in DNCB–treated Balb/c mice by suppressing the synthesis of inflammatory mediators such as TNF-α and Ig-E. Taken together, this study suggested that compound 23 could be an effective PDE4 inhibitor for the potential treatment of AD.