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

Base Information

• Chemical Name: Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate
• CAS No.: 776-53-4
• Molecular Formula: C8H11N3O2S
• Molecular Weight: 213.26
• Hs Code.: 29335990
• European Community (EC) Number: 668-974-5
• NSC Number: 9310
• DSSTox Substance ID: DTXSID30278699
• Nikkaji Number: J3.019.844A
• Wikidata: Q72472514
• ChEMBL ID: CHEMBL1713273
• Mol file: 776-53-4.mol

Synonyms:776-53-4;Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate;Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate;ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate;ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate;MFCD00090781;4-Amino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester;MLS000554777;4-amino-2-(methylthio)-5-pyrimidinecarboxylic acid ethyl ester;SMR000146894;5-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl ester;2-methylthio-5-ethoxycarbonyl-4-aminopyrimidine;ethyl 4-amino-2-(methylsulfanyl)-5-pyrimidinecarboxylate;NSC9310;ChemDiv3_014680;4-Amino-2-(methylthio)-;SCHEMBL256224;cid_222666;CHEMBL1713273;ethyl 4-amino-2-methylsulfanyl-pyrimidine-5-carboxylate;BDBM55426;DTXSID30278699;HMS1514L06;HMS2305K19;BCP23040;NSC 9310;NSC-9310;BBL004250;STL140273;AKOS001086755;CCG-164998;CS-W008025;GS-5700;IDI1_030478;AC-23450;BL000129;SY023719;AM20100772;BB 0242855;FT-0650706;EN300-11207;AF-601/00276042;J-520963;Ethyl 4-amino-2-(methylthio)-pyrimidine-5-carboxylate;Ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate;ethyl 4-amino-2-methylsulfanyl-5-pyrimidinecarboxylate;Z24688043;ethyl 4-amino-2-methylsulfanyl-5-pyrimidine carboxylate;ethyl 4-azanyl-2-methylsulfanyl-pyrimidine-5-carboxylate;2-(Methylthio)-4-aminopyrimidine-5-carboxylic acid ethyl ester;4-amino-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester;4-Amino-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester;4-Amino-2-methylsulfanyl-pyrimidine-5-carbo xylic acid ethyl ester;Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 1.11E-05mmHg at 25°C
• Melting Point: 127-128 °C
• Refractive Index: 1.585
• Boiling Point: 370.3 °C at 760 mmHg
• PKA: 2.46±0.10(Predicted)
• Flash Point: 177.8 °C
• PSA: 103.40000
• Density: 1.31 g/cm³
• LogP: 1.53860
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 213.05719778
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Amino-2-(methylthio)-5-pyrimidinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(N=C1N)SC
• Uses: Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate is used for preparation of pyrimidopyrimidines as protein kinase inhibitors.

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

There total 9 articles about Ethyl 4-amino-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: 86.0%

2,6-Dichlorobenzaldehyde 4-<2-Cyano-2-(ethoxycarbonyl)vinyl>3-methylisothiosemicarbazone (78514-86-0) → ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate (776-53-4) + 2,6-dichloro-benzonitrile (1194-65-6) + Ethyl 2-(2,6-Dichlorophenyl)-5-(methylthio)<1,2,4>triazolo<1,5-c>pyrimidine-8-carboxylate (78514-99-5)

Guidance literature:

In pyridine; for 1h; Heating;

DOI:10.1021/jo00333a005

Reference yield: 55.6%

C15H15N5O4S (78514-89-3) → ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate (776-53-4) + Ethyl 5-(Methylthio)-2-(m-nitrophenyl)<1,2,4>triazolo<1,5-c>pyrimidine-8-carboxylate (78515-02-3) + 3-nitrobenzonitrile (619-24-9)

Guidance literature:

In pyridine; for 1h; Product distribution; Mechanism; Heating;

DOI:10.1021/jo00333a005

Reference yield: 35.6%

C16H18N4O3S (78514-87-1) → ethyl 4-amino-2-methylmercaptopyrimidine-5-carboxylate (776-53-4) + 2-methoxy-benzonitrile (6609-56-9) + Ethyl 2-(o-Methoxyphenyl)-5-(methylthio)<1,2,4>triazolo<1,5-c>pyrimidine-8-carboxylate (78515-00-1)

Guidance literature:

In pyridine; for 1h; Product distribution; Mechanism; Heating;

DOI:10.1021/jo00333a005

upstream raw materials:

ethyl 4-amino-2-thioxo-1H-pyrimidine-5-carboxylate

dimethyl sulfate

benzaldehyde 3-methyl-4-<2-cyano-2-(ethoxycarbonyl)vinyl>isothiosemicarbazone

C₁₅H₁₅ClN₄O₂S

Downstream raw materials:

ethyl 3-(4-amino-2-(methylthio)pyrimidin-5-yl)acrylate

4-amino-2-methylthiopyrimidine-5-carboxamide

Refernces

• 1、 Yamazaki, Chiji. "Cyclization of Isothiosemicarbazones. 5. Triazolopyrimidines". . p. 3956 - 3959. Retrieved 2007/10/02.