3073-77-6

Basic information

• Product Name: 2-Amino-5-nitropyrimidine
• Synonyms: 2-AMINO-5-NITROPYRIMIDINE;TIMTEC-BB SBB004166;2-Pyrimidinamine, 5-nitro-;5-Nitro-2-pyrimidinamine;5-nitropyrimidin-2-ylamine;5-nitropyrimidin-2-amine;2-Amino-5-nitropyrimidine, 97+%;2-Pyrimidinamine, 5-nitro- (9CI)
• CAS NO: 3073-77-6
• Molecular Formula: C₄H₄N₄O₂
• Molecular Weight: 140.1
• EINECS: 221-348-1
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidines;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 3073-77-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 235-237 °C(lit.)
• Boiling Point: 256.57°C (rough estimate)
• Flash Point: 197.1 °C
• Appearance: Light yellow/Fine Crystalline Powder
• Density: 1.5799 (rough estimate)
• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.8010 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Dimethylformamide
• PKA: 0.04±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-nitropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-nitropyrimidine(3073-77-6)
• EPA Substance Registry System: 2-Amino-5-nitropyrimidine(3073-77-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3073-77-6(Hazardous Substances Data)

Usage

Chemical Properties

light yellow fine crystalline powder

InChI:InChI=1/C4H4N4O2/c5-4-6-1-3(2-7-4)8(9)10/h1-2H,(H2,5,6,7)

Upstream product

• 5329-33-9 o-methylisourea hydrochloride 
• 14080-32-1 5-nitropyrimidine 
• 10320-42-0 2-Chloro-5-nitropyrimidine 
• 593-85-1 diguanidine carbonate 
• 609-32-5 2-nitromalonaldehyde 

Downstream Products

• 22715-27-1 pyrimidine-2,5-diamine 
• 3264-10-6 5-nitro-2(1H)-pyrimidinone 
• 50840-23-8 5-methylpyrimidin-2-amine 
• 100-15-2 N-methyl(p-nitroaniline) 
• 910907-13-0 N₂-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,5-diamine 
• 26806-72-4 (4-methoxy-phenyl)-(5-nitro-pyrimidin-2-yl)-amine 
• 331809-06-4 3-chloro-4-fluoro-N-(5-nitropyrimidin-2-yl)benzamide 
• 10320-42-0 2-Chloro-5-nitropyrimidine 
• 910907-48-1 4-[4-(5-nitro-pyrimidin-2-ylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1458220-81-9 N-(5-nitropyrimidin-2-yl)-2-(trifluoromethyl)benzamide 
• 1458220-82-0 N-(5-nitropyrimidin-2-yl)-4-(trifluoromethyl)benzamide 
• 331806-98-5 2-(N-benzoyl)-amino-5-amino-pyrimidine 
• 331806-93-0 2-(N-benzoyl)amino-5-nitropyrimidine 
• 910905-25-8 4-(5-nitropyrimidin-2-ylamino)-N-(2-hydroxyethyl)-N-isopropylbenzamide 

Relevant articles and documents

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.

Ring Transformations in Reactions of Heterocyclic Compounds with Nucleophiles. Conversion of 5-Nitropyrimidine into 2-Substituted 5-Nitropyrimidine and 2-Amino-5-nitropyridines by Amidines

The reaction of 5-nitropyrimidine (1) with benzamidine, pivalamidine, acetamidine, propionamidine, α-phenylacetamidine, O-methylisourea hydrochlorides, and cyanamide in ethanolic solution in the presence of triethylamine has been investigated.It was found that reaction of 1 with alkyl(aryl) amidines, having no active methylene groups attached to the amidine moiety (pivalamidine, benzamidine), exclusively formed the corresponding 2-substituted 5-nitropyrimidines in good yields.With acetamidine and propionamidine, in addition to the formation of the 2-substituted 5-nitropyrimidines, the formation of 2-amino-5-nitropyridines also was observed; with α-phenylacetamidine a 2-amino-5-nitropyridine derivative exclusively was obtained.The reaction of 1 with both O-methylisourea and cyanamide leads to 2-amino-5-nitropyrimidine.These reactions provide new examples of degenerate ring transformations of the pyrimidine ring system and of the ring transformation of pyrimidines into pyridines.