2-Chloro-4-(methylthio)pyrimidine

Base Information

• Chemical Name: 2-Chloro-4-(methylthio)pyrimidine
• CAS No.: 49844-93-1
• Molecular Formula: C5H5ClN2S
• Molecular Weight: 160.627
• Hs Code.: 29335990
• European Community (EC) Number: 638-935-7
• DSSTox Substance ID: DTXSID60586052
• Wikidata: Q82478080
• Mol file: 49844-93-1.mol

Synonyms:2-Chloro-4-(methylthio)pyrimidine;49844-93-1;2-Chloro-4-methylthiopyrimidine;2-Chloro-4-methylsulfanylpyrimidine;2-Chloro-4-methylsulfanyl-pyrimidine;2-chloro-4-(methylsulfanyl)pyrimidine;MFCD09265490;Pyrimidine, 2-chloro-4-(methylthio)-;Pyrimidine,2-chloro-4-(methylthio)-;SCHEMBL1984295;DTXSID60586052;VAATWVRXPRDPPM-UHFFFAOYSA-N;AMY11450;AKOS011627927;CS-W005463;PS-3826;SB57339;AC-26657;SY024250;2-chloro-4-methylthiopyrimidine, AldrichCPR;A7413;EN300-246065;J-508695;Z976663640

Chemical Property of 2-Chloro-4-(methylthio)pyrimidine

Chemical Property:

• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.594
• Boiling Point: 308.3 °C at 760 mmHg
• PKA: -0.45±0.20(Predicted)
• Flash Point: 140.3 °C
• PSA: 51.08000
• Density: 1.37 g/cm³
• LogP: 1.85190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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

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

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=NC(=NC=C1)Cl

Technology Process of 2-Chloro-4-(methylthio)pyrimidine

There total 4 articles about 2-Chloro-4-(methylthio)pyrimidine 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: 80.0%

2,6-Dichloropyrimidine (3934-20-1) + sodium thiomethoxide (5188-07-8) → 2-chloro-4-(methylsulfanyl)pyrimidine (49844-93-1)

Guidance literature:

With water; In tetrahydrofuran; at -10 - 20 ℃;

DOI:10.1002/jhet.5570440437

Reference yield: 75.0%

2-chloropyrimidine (1722-12-9,1195939-87-7) + methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) → 2-chloro-4-(methylsulfanyl)pyrimidine (49844-93-1)

Guidance literature:

2-chloropyrimidine; With N-tetramethylpiperidine magnesium chloride; lithium chloride; In tetrahydrofuran; at -55 ℃; for 2h;

methanethiosulfonic acid S-methyl ester; In tetrahydrofuran; at -55 ℃;

DOI:10.1002/anie.200504024

Reference yield:

4-methylsulfanyl-1H-pyrimidine-2-thione (51674-12-5) → 2-chloro-4-(methylsulfanyl)pyrimidine (49844-93-1)

Guidance literature:

With trichlorophosphate;

upstream raw materials:

4-methylsulfanyl-1H-pyrimidine-2-thione

2-chloropyrimidine

methanethiosulfonic acid S-methyl ester

2,6-Dichloropyrimidine

Downstream raw materials:

4-(methylsulfonyl)-N-phenylpyrimidin-2-amine

5-fluoro-3-(4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

4-[5-(3-methyl-5-{[4-(methylsulfanyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

4-[5-(3-methyl-5-{[4-(methylsulfinyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

Refernces

• 1、 Smith, Sean M.,Buchwald, Stephen L.. "Regioselective 2-Amination of Polychloropyrimidines". supporting information. p. 2180 - 2183. Retrieved 2016/06/01.
• 2、 -. "SUBSTITUTED PYRIMIDINE COMPOUNDS AND THEIR USE AS SYK INHIBITORS". Page/Page column 63. . Retrieved 2013/07/31.