2627-52-3

Basic information

• Product Name: Pyrimidine, 2-(methylthio)-4-phenyl-6-(trifluoromethyl)-
• CAS NO: 2627-52-3
• Molecular Formula: C12H9F3N2S
• Molecular Weight: 270.278
• Mol File: 2627-52-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Pyrimidine, 2-(methylthio)-4-phenyl-6-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 2-(methylthio)-4-phenyl-6-(trifluoromethyl)-(2627-52-3)
• EPA Substance Registry System: Pyrimidine, 2-(methylthio)-4-phenyl-6-(trifluoromethyl)-(2627-52-3)

Safety Data

• Hazardous Substances Data: 2627-52-3(Hazardous Substances Data)

Upstream product

• 191341-06-7 2-methylthio-4-trifluoromethyl-4-iodopyrimidine 
• 98-80-6 phenylboronic acid 
• 98-86-2 acetophenone 
• 147895-43-0 S-methylisothiourea hemisulphate 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 16097-62-4 4-hydroxy-2-(methylthio)-6-(trifluoromethyl)pyrimidine 
• 136547-20-1 2-(methylthio)-4-(trifluoromethyl)pyrimidine 

Downstream Products

• 2627-54-5 2-(methylsulfonyl)-4-phenyl-6-(trifluoromethyl)pyrimidine 

Relevant articles and documents

Further hit optimization of 6-(trifluoromethyl)pyrimidin-2-amine based TLR8 modulators: Synthesis, biological evaluation and structure–activity relationships

Toll-like receptor 8 (TLR8) is an endosomal TLR that has an important role in the innate human immune system, which is involved in numerous pathological conditions. Excessive activation of TLR8 can lead to inflammatory and autoimmune diseases, which highlights the need for development of TLR8 modulators. However, only a few small-molecule modulators that selectively target TLR8 have been developed. Here, we report the synthesis and systematic investigation of the structure–activity relationships of a series of novel TLR8 negative modulators based on previously reported 6-(trifluoromethyl)pyrimidin-2-amine derivatives. Four compounds showed low-micromolar concentration-dependent inhibition of TLR8-mediated signaling in HEK293 cells. These data confirm that the 6-trifluoromethyl group and two other substituents on positions 2 and 4 are important structural elements of pyrimidine-based TLR8 modulators. Substitution of the main scaffold at position 2 with a methylsulfonyl group or para hydroxy/hydroxymethyl substituted benzylamine is essential for potent negative modulation of TLR8. Our best-in-class TLR8-selective modulator 53 with IC50 value of 6.2 μM represents a promising small-molecule chemical probe for further optimization to a lead compound with potent immunomodulatory properties.

Synthesis and Metalation of Trifluoromethylpyrimidines. Metalation of Diazines. XVI

A new route to trifluoromethylpyrimidines is described.Lithiation of trifluoromethylpyrimidines was successfully achieved and was used to synthesize new pyrimidine derivatives.A new synthetic route to a biologically active molecule with antimycotic activi