103906-34-9

Basic information

• Product Name: 7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE
• Synonyms: 7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE;7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-YLAMINE
• CAS NO: 103906-34-9
• Molecular Formula: C₁₁H₉N₅
• Molecular Weight: 211.22
• Mol File: 103906-34-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE(103906-34-9)
• EPA Substance Registry System: 7-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-2-AMINE(103906-34-9)

Safety Data

• Hazardous Substances Data: 103906-34-9(Hazardous Substances Data)

Upstream product

• 1455-77-2 guanazole 
• 68-12-2 N,N-dimethyl-formamide 
• 98-86-2 acetophenone 
• 13788-90-4 3,3-dimethoxy-1-phenylpropan-1-one 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 1455-77-2 guanazole 
• 100-52-7 benzaldehyde 
• 121-44-8 triethylamine 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 

Relevant articles and documents

Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment

A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.

1,2,4-Triazolo[1,5-a]pyrimidines: Efficient one-step synthesis and functionalization as influenza polymerase PA-PB1 interaction disruptors

In the search for new anti-influenza virus (IV) compounds, we have identified the 1,2,4-triazolo[1,5-a]pyrimidine (TZP) as a very suitable scaffold to obtain compounds able to disrupt IV RNA-dependent RNA polymerase (RdRP) PA-PB1 subunits heterodimerization. In this work, in order to acquire further SAR insights for this class of compounds and identify more potent derivatives, we designed and synthesized additional series of analogues to investigate the role of the substituents around the TZP core. To this aim, we developed four facile and efficient one-step procedures for the synthesis of 5-phenyl-, 6-phenyl- and 7-phenyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidines, and 2-amino-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol. Two analogues having the ethyl carboxylate moiety at the C-2 position of the TZP were also prepared in good yields. Then, the scaffolds herein synthesized and two previous scaffolds were functionalized and evaluated for their anti-IAV activity, leading to the identification of compound 22 that showed both anti-PA-PB1 (IC50 = 19.5 μM) and anti-IAV activity (EC50 = 16 μM) at non-toxic concentrations, thus resulting among the most active TZP derivatives reported to date by us. A selection of the synthesized compounds, along with a set of in-house available analogues, was also tested against SARS-CoV-2. The most promising compound 49 from this series displayed an EC50 value of 34.47 μM, highlighting the potential of the TPZ scaffold in the search for anti-CoV agents.

Triazolopyridines as selective JAK1 inhibitors: From hit identification to GLPG0634

Janus kinases (JAK1, JAK2, JAK3, and TYK2) are involved in the signaling of multiple cytokines important in cellular function. Blockade of the JAK-STAT pathway with a small molecule has been shown to provide therapeutic immunomodulation. Having identified