4-Chloro-2-methylthiopyrimidine

Base Information

• Chemical Name: 4-Chloro-2-methylthiopyrimidine
• CAS No.: 49844-90-8
• Molecular Formula: C5H5ClN2S
• Molecular Weight: 160.627
• Hs Code.: 29335990
• European Community (EC) Number: 256-500-6
• NSC Number: 100866
• DSSTox Substance ID: DTXSID60198114
• Nikkaji Number: J240.165G
• Wikidata: Q72455400
• Mol file: 49844-90-8.mol

Synonyms:49844-90-8;4-Chloro-2-methylthiopyrimidine;4-Chloro-2-(methylthio)pyrimidine;4-chloro-2-methylsulfanylpyrimidine;4-Chloro-2-methylsulfanyl-pyrimidine;4-chloro-2-(methylsulfanyl)pyrimidine;pyrimidine, 4-chloro-2-(methylthio)-;C5H5ClN2S;4-chloro-2-(methylthio) pyrimidine;EINECS 256-500-6;MFCD00006083;NSC100866;NCIOpen2_001949;SCHEMBL18947;C5-H5-Cl-N2-S;2-methylthio-4-chloropyrimidine;6-Chloro-2-methylthiopyrimidine;2-methylthio-4-chloro pyrimidine;2-methylthio-4-chloro-pyrimidine;4-chloro -2-methylthiopyrimidine;4-chloro-2-methylthio-pyrimidine;DTXSID60198114;2-Methylmercapto-6-chlorpyrimidin;2-(methylthio)-4-chloropyrimidine;2-methylmercapto-4-chloropyrimidine;BCP27066;CS-M3277;AKOS005255070;4-Chloro-2-methylthiopyrimidine, 98%;NSC 100866;NSC-100866;PB10012;PS-5742;AC-25659;A7412;AM20100220;C3087;FT-0617987;EN300-94700;J-514907;W-202873;Z1255485306;4-chloro-2-(methylthio)pyrimidine;4-CHLORO-2-METHYLSULFANYLPYRIMIDINE

Chemical Property of 4-Chloro-2-methylthiopyrimidine

Chemical Property:

• Appearance/Colour: Clear yellow to brown liquid
• Vapor Pressure: 0.0511mmHg at 25°C
• Melting Point: -2 °C(lit.)
• Refractive Index: n20/D 1.6(lit.)
• Boiling Point: 243.1 °C at 760 mmHg
• PKA: -0.56±0.20(Predicted)
• Flash Point: 100.8 °C
• PSA: 51.08000
• Density: 1.37 g/cm³
• LogP: 1.85190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Hygroscopic
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 159.9861970
• Heavy Atom Count: 9
• Complexity: 91

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-2-(methylthio)pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=NC=CC(=N1)Cl
• Uses: It finds it application as a building block used in medicinal chemistry synthesis. 4-Chloro-2-methylthiopyrimidine is used in the total synthesis of the marine alkaloid variolin B1 and 2-hydroxy-4-pyrimidinecarboxylic acid. It is also used in the synthesis of 2,4-disubstituted pyrimidines, a novel class of KDR kinase inhibitors. 4-Chloro-2-methylthiopyrimidine was used in the total synthesis of the marine alkaloid variolin B1 and 2-hydroxy-4-pyrimidinecarboxylic acid. It was used in the synthesis of 2,4-disubstituted pyrimidines, a novel class of KDR kinase inhibitors. It was used as building block in medicinal chemistry synthesis.

Technology Process of 4-Chloro-2-methylthiopyrimidine

There total 5 articles about 4-Chloro-2-methylthiopyrimidine 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: 88.3%

2-(methylsulfanyl)pyrimidin-4-ol (5751-20-2,124700-70-5) → 4-Chloro-2-methylthiopyrimidine (49844-90-8)

Guidance literature:

2-(methylsulfanyl)pyrimidin-4-ol; With trichlorophosphate; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 0.5h;

With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20 - 80 ℃; for 1h; Time; Solvent; Reagent/catalyst;

Reference yield: 87.6%

2-Methylthiouracil (5751-20-2,124700-69-2) → 4-Chloro-2-methylthiopyrimidine (49844-90-8)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 40 ℃; for 3h;

DOI:10.1177/1747519819831858

Reference yield:

→ 4-Chloro-2-methylthiopyrimidine (49844-90-8)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate;

upstream raw materials:

2-Methylthiouracil

2-methylthio-1H-pyrimidin-4-one

2-(methylsulfanyl)pyrimidin-4-ol

Downstream raw materials:

4-(4-methoxyphenyl)-2-(methylsulfanyl)pyrimidine

4-methoxy-2-(methylthio)pyrimidine

2-(methylsulfanyl)-4-phenylpyrimidine

4-tert-butyldiphenylsilyloxymethyl-2-methylthiopyrimidine

Refernces

• 1、 Li, Shu-ting,Chen, Jun-qing,Feng, Cheng-liang,Yang, Wan-feng,Ji, Min. "A new route for the synthesis of Palbociclib". . p. 3043 - 3051. Retrieved 2019/10/19.
• 2、 Aldobaev,Prezent,Zavarzin. "Synthesis of N,N-dialkyl-1-(2-alkylthiopyrimidin-4-yl)piperidin- 4-amines as potential heat shock protein inhibitors". . p. 2127 - 2130. Retrieved 2019/01/08.