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

Base Information

• Chemical Name: Ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate
• CAS No.: 53554-29-3
• Molecular Formula: C8H10N2O3S
• Molecular Weight: 214.245
• Hs Code.: 2933599090
• European Community (EC) Number: 633-406-7
• NSC Number: 43816
• DSSTox Substance ID: DTXSID80286103
• Nikkaji Number: J1.499.966C
• Wikidata: Q72475281
• Mol file: 53554-29-3.mol

Synonyms:53554-29-3;ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate;Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate;1,4-DIHYDRO-2-(METHYLTHIO)-4-OXO-5-PYRIMIDINE-CARBOXYLATE ACID ETHYL ESTER;ethyl 2-methylsulfanyl-6-oxo-1H-pyrimidine-5-carboxylate;ethyl 1,4-dihydro-2-(methylthio)-4-oxopyrimidine-5-carboxylate;1,4-dihydro-2-(methylthio)-4-oxo-5-pyrimidinecarboxylic acid ethyl ester;1,4-Dihydro-2-(Methylthio)-4-Oxo-5-Pyrimidine-Carboxylic Acid Ethyl Ester;NSC 43816;ethyl 2-(methylsulfanyl)-4-oxo-1,4-dihydropyrimidine-5-carboxylate;Ethyl 1,4-dihydro-2-(methylthio)-4-oxo-5-pyrimidinecarboxylate;ethyl 2-(methylthio)-4-oxo-1,4-dihydropyrimidine-5-carboxylate;Ethyl 4-Hydroxy-2-Methylthio-5-Pyrimidinecarboxylate;NSC43816;NCIOpen2_007256;PotassiumPhenyltrifluoroborate;SCHEMBL1628253;SCHEMBL15015768;DTXSID80286103;BCP23045;4-hydroxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester;MFCD00023234;MFCD00194960;MFCD03002357;NSC-43816;2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester;AKOS000270865;AKOS000320069;AKOS015996018;CCG-165042;CS-W002133;GS-5926;PS-3226;SB60579;SY018371;AM20100316;EU-0009282;FT-0640172;2-Methylthio-5-ethoxycarbonyl-4-hydroxypyrimidine;SR-01000076764;5-ethoxycarbonyl-2-(methylthio)pyrimidin-4(1H)-one;ethyl 2-methylthio-4-hydroxypyrimidine-5-carboxylate;J-520509;SR-01000076764-1;ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate;Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate;Ethyl 1,6-dihydro-2-methylthio-6-oxo-5pyrimidinecarboxylate;ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrmidine-5-carboxylate;Ethyl 2-(methylthio)-6-oxo-1,6-dihyropyrimidine-5-carboxylate;ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate;4-hydroxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester;4-Hydroxy-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester;ethyl 2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate;Ethyl 2-Methylsulfanyl-4-oxo-1,4-dihydro-pyrimidine-5-carboxylate

Chemical Property of Ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate

Chemical Property:

• Vapor Pressure: 4.37E-05mmHg at 25°C
• Melting Point: 136-144°C
• Refractive Index: 1.601
• Boiling Point: 340.4 °C at 760 mmHg
• PKA: 6.48±0.50(Predicted)
• Flash Point: 159.7 °C
• PSA: 97.61000
• Density: 1.37g/cm³
• LogP: 1.08080
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 214.04121336
• Heavy Atom Count: 14
• Complexity: 323

Purity/Quality:

99.9% ^*data from raw suppliers

1,4-Dihydro-2-(methylthio)-4-oxo-5-pyrimidine-carboxylateacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(NC1=O)SC
• 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.

Technology Process of Ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate

There total 12 articles about Ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate 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: 99.7%

carbamimidothioic acid methyl ester (2986-19-8) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (53554-29-3)

Guidance literature:

carbamimidothioic acid methyl ester; With sodium hydroxide; In ethanol; for 0.5h;

diethyl 2-ethoxymethylenemalonate; In ethanol; at 20 ℃; for 10h; Time;

Reference yield: 82.0%

diethyl ethoxymalonate (37555-99-0) + S-Methylisothiourea sulfate (867-44-7,147895-43-0) → ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (53554-29-3)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h; Reflux;

Reference yield: 81.0%

S-methylisothiourea hemisulphate (147895-43-0) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate (53554-29-3)

Guidance literature:

S-methylisothiourea hemisulphate; With ethanol; sodium ethanolate; at 0 ℃; Inert atmosphere;

diethyl 2-ethoxymethylenemalonate; In ethanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.01.092

upstream raw materials:

ethyl 4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxilate

dimethyl sulfate

carbamimidothioic acid methyl ester

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

2-dimethylamino-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

2-methylamino-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

6-Oxo-2-o-tolylamino-1,6-dihydro-pyrimidine-5-carboxylic acid

Refernces

• 1、 Purushothaman, Baskaran,Arumugam, Parthasarathy,Kulsi, Goutam,Song, Joon Myong. "Design, synthesis, and biological evaluation of novel catecholopyrimidine based PDE4 inhibitor for the treatment of atopic dermatitis". supporting information. p. 673 - 690. Retrieved 2018/01/26.
• 2、 Wang, Shi-Chun,Wan, Fu-Xian,Liu, Si,Zhang, Shuai,Jiang, Lin. "Synthesis and Antifungal Activity Evaluation of Novel Substituted Pyrimidine-5-Carboxamides Bearing the Pyridine Moiety". . p. 445 - 451. Retrieved 2018/01/15.