Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate

Base Information

• Chemical Name: Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
• CAS No.: 5909-24-0
• Molecular Formula: C8H9ClN2O2S
• Molecular Weight: 232.691
• Hs Code.: 29339900
• European Community (EC) Number: 227-619-0
• NSC Number: 123534
• UNII: 3EZY6B6CLY
• DSSTox Substance ID: DTXSID20207832
• Nikkaji Number: J124.092G
• Wikidata: Q72473705
• Mol file: 5909-24-0.mol

Synonyms:4-chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester;ethyl 4-chloro-MPC

Chemical Property of Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate

Chemical Property:

• Appearance/Colour: off white to light yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 60-63 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 335.7 °C at 760 mmHg
• PKA: -2.19±0.29(Predicted)
• Flash Point: 156.83 °C
• PSA: 77.38000
• Density: 1.37 g/cm³
• LogP: 2.02860
• Storage Temp.: Keep Cold
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 232.0073264
• Heavy Atom Count: 14
• Complexity: 206

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl 4-Chloro-2-methylthiopyrimidine-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(N=C1Cl)SC
• Uses: A pyrimidine derivative as inhibitor of Streptococcus faecium, Lactobacillus casei, and Pediococcus cerevisiae Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate was used in the synthesis of pyrimidinopyridones, potential inhibitors of the FMS tyrosine kinase.

Technology Process of Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate

There total 5 articles about Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (53554-29-3) → 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0)

Guidance literature:

With thionyl chloride; at 60 ℃; for 3h;

Reference yield: 84.5%

sodium 5-(ethoxycarbonyl)-2-(methylthio)-4-oxo-4H-pyrimidin-3-ide → 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0)

Guidance literature:

sodium 5-(ethoxycarbonyl)-2-(methylthio)-4-oxo-4H-pyrimidin-3-ide; With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20 - 30 ℃; for 0.5h; Large scale;

With trichlorophosphate; In N,N-dimethyl-formamide; toluene; at 55 - 65 ℃; for 1.5h; Large scale;

Reference yield:

ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate (53554-29-3) → 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0)

Guidance literature:

With thionyl chloride;

DOI:10.1021/ja01243a015

upstream raw materials:

ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

2-methanesulfanyl-4-phenylamino-pyrimidine-5-carboxylic acid ethyl ester

4-ethylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

4-cyclopentylamino-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester

Refernces

• 1、 -. "4 - Chloro -2 - a sulfur pyrimidine -5 - carboxylic acid ethyl ester". Paragraph 0028; 0029; 0030; 0031; 0032; 0033. . Retrieved 2019/05/11.
• 2、 -. "Method for synthesizing high-purity 4-chloro-2-methylthiopyrimidine-5-ethyl carboxylate". Paragraph 0015-0018. . Retrieved 2018/06/26.