4-Chloro-6-methylthieno[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-Chloro-6-methylthieno[2,3-d]pyrimidine
• CAS No.: 106691-21-8
• Molecular Formula: C7H5ClN2S
• Molecular Weight: 184.649
• Hs Code.: 2934999090
• European Community (EC) Number: 674-842-8
• DSSTox Substance ID: DTXSID40374015
• Wikidata: Q72455351
• Mol file: 106691-21-8.mol

Synonyms:4-chloro-6-methylthieno[2,3-d]pyrimidine;106691-21-8;Thieno[2,3-d]pyrimidine, 4-chloro-6-methyl-;MFCD03030440;SCHEMBL1368716;DTXSID40374015;STL582255;AKOS000281317;PB27587;AM802885;AS-41806;SY045456;4-chloro-6-methyl thieno[2,3-d]pyrimidine;4-chloro-6-methyl-thieno[2,3-d]pyrimidine;CS-0050898;FT-0725343;EN300-71589;A26212;4-Chloro-6-methylthieno[2,3-d]pyrimidine, AldrichCPR;Z1142685199

Chemical Property of 4-Chloro-6-methylthieno[2,3-d]pyrimidine

Chemical Property:

• Vapor Pressure: 0.0019mmHg at 25°C
• Melting Point: 88-91℃ (sublm)
• Refractive Index: 1.682
• Boiling Point: 301.3 °C at 760 mmHg
• Flash Point: 136 °C
• PSA: 54.02000
• Density: 1.445 g/cm³
• LogP: 2.65310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 183.9861970
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

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

4-Chloro-6-methylthieno[2,3-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(S1)N=CN=C2Cl

Technology Process of 4-Chloro-6-methylthieno[2,3-d]pyrimidine

There total 5 articles about 4-Chloro-6-methylthieno[2,3-d]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: 82.0%

6-Methylthieno<2,3-d>pyrimid-4-one (108831-66-9) → 4-chloro-6-methylthieno<2,3-d>pyrimidine (106691-21-8)

Guidance literature:

With N,N-dimethyl-formamide; trichlorophosphate; In 1,2-dichloro-ethane; for 1.5h; Heating;

DOI:10.1007/BF00765112

Reference yield:

Langlois reagent (2926-29-6) + 6-Methylthieno<2,3-d>pyrimid-4-one (108831-66-9) → 4-chloro-6-methylthieno<2,3-d>pyrimidine (106691-21-8)

Guidance literature:

With tert.-butylhydroperoxide; trifluoroacetic acid; In chloroform; water; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2019.126751

Reference yield:

ethyl 2-amino-5-methylthiophene-3-carboxylate (4815-32-1) → 4-chloro-6-methylthieno<2,3-d>pyrimidine (106691-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / 2 h / Heating

2: 82 percent / phosphorus oxychloride, DMF / 1,2-dichloro-ethane / 1.5 h / Heating

With N,N-dimethyl-formamide; trichlorophosphate; In 1,2-dichloro-ethane;

DOI:10.1007/BF00765112

upstream raw materials:

6-Methylthieno<2,3-d>pyrimid-4-one

ethyl 2-amino-5-methylthiophene-3-carboxylate

Langlois reagent

Downstream raw materials:

6-methylthieno<2,3-d>pyrimidine

6-Bromomethyl-4-chlorothieno<2,3-d>pyrimidine

C₇H₈N₄S

[(6-methylthieno[2,3-d]pyrimidin-4-yl)thio]acetic acid

Refernces

• 1、 Atkinson, Benjamin N.,Bayle, Elliott D.,Bictash, Magda,Fish, Paul V.,Frew, Sarah,Jeganathan, Fiona,Jones, E. Yvonne,Mahy, William,Monaghan, Amy,Papageorgiou, George,Sipthorp, James,Steadman, David,Svensson, Fredrik,Zhao, Yuguang. "Scaffold-hopping identifies furano[2,3-d]pyrimidine amides as potent Notum inhibitors". supporting information. . Retrieved 2020/01/03.
• 2、 Tarver, James E.,Pabba, Praveen K.,Barbosa, Joseph,Han, Qiang,Gardyan, Michael W.,Brommage, Robert,Thompson, Andrea Y.,Schmidt, James M.,Wilson, Alan G.E.,He, Wei,Lombardo, Victoria K.,Carson, Kenneth G.. "Stimulation of cortical bone formation with thienopyrimidine based inhibitors of Notum Pectinacetylesterase". . p. 1525 - 1528. Retrieved 2016/07/27.