26806-61-1

Basic information

• Product Name: (5-nitro-pyrimidin-2-yl)-phenyl-amine
• Synonyms: (5-nitro-pyrimidin-2-yl)-phenyl-amine
• CAS NO: 26806-61-1
• Molecular Weight: 216.199
• Mol File: 26806-61-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5-nitro-pyrimidin-2-yl)-phenyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (5-nitro-pyrimidin-2-yl)-phenyl-amine(26806-61-1)
• EPA Substance Registry System: (5-nitro-pyrimidin-2-yl)-phenyl-amine(26806-61-1)

Safety Data

• Hazardous Substances Data: 26806-61-1(Hazardous Substances Data)

Upstream product

• 10320-42-0 2-Chloro-5-nitropyrimidine 
• 62-53-3 aniline 

Downstream Products

• 1613228-38-8 2-methyl-N-(2-(phenylamino)pyrimidin-5-yl)-5-(3-(trifluoromethyl)benzamido)benzamide 
• 26806-71-3 N²-phenyl-pyrimidine-2,5-diamine 

Relevant articles and documents

One-Pot Protocol to Synthesize 2-Aminophenols from Anilines via Palladium-Catalyzed C-H Acetoxylation

This paper describes a facile one-pot protocol to synthesize 2-aminophenol derivatives via a palladium-catalyzed C-H acetoxylation strategy with 5-nitropyrimidine as a directing group (DG), which can be easily preinstalled and readily removed under mild condition after the coupling. In addition, the transformation is operationally simple, has high functional group tolerance, and is amenable to gram-scale. Moreover, several examples were shown that introduction/removal of 5-nitropyrimidine and the C-H oxylation sequence could be integrated in one pot.

Discovery of a series of 2,5-diaminopyrimidine covalent irreversible inhibitors of Bruton's tyrosine kinase with in vivo antitumor activity

Bruton's tyrosine kinase (Btk) is an attractive drug target for treating several B-cell lineage cancers. Ibrutinib is a first-in-class covalent irreversible Btk inhibitor and has demonstrated impressive effects in multiple clinical trials. Herein, we present a series of novel 2,5-diaminopyrimidine covalent irreversible inhibitors of Btk. Compared with ibrutinib, these inhibitors exhibited a different selectivity profile for the analyzed kinases as well as a dual-action mode of inhibition of both Btk activation and catalytic activity, which counteracts a negative regulation loop for Btk. Two compounds from this series, 31 and 38, showed potent antiproliferative activities toward multiple B-cell lymphoma cell lines, including germinal center B-cell-like diffuse large B cell lymphoma (GCB-DLBCL) cells. In addition, compound 31 significantly prevented tumor growth in a mouse xenograft model.