143504-99-8

Basic information

• Product Name: 4(3H)-Pyrimidinone, 2,6-diamino- (9CI)
• Synonyms: 4(3H)-Pyrimidinone, 2,6-diamino- (9CI);2,4-Diamino-1,6-dihydro-6-oxopyrimidine;2,6-Diaminopyrimidin-4(3H)-one
• CAS NO: 143504-99-8
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.11664
• Product Categories: PYRIMIDINE
• Mol File: 143504-99-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4(3H)-Pyrimidinone, 2,6-diamino- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4(3H)-Pyrimidinone, 2,6-diamino- (9CI)(143504-99-8)
• EPA Substance Registry System: 4(3H)-Pyrimidinone, 2,6-diamino- (9CI)(143504-99-8)

Safety Data

• Hazardous Substances Data: 143504-99-8(Hazardous Substances Data)

Usage

General Description

4(3H)-Pyrimidinone, 2,6-diamino- (9CI) is a chemical compound with the molecular formula C4H6N4O. It is a pyrimidine derivative, which is a heterocyclic organic compound that is widely found in nature and has various biological activities. This specific compound has a 2,6-diamino substitution pattern on the pyrimidine ring, and it is known for its potential as an antiviral and antitumor agent. It has also been studied for its potential use in the treatment of various diseases, including cancer and viral infections. Additionally, it has been used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Overall, 4(3H)-Pyrimidinone, 2,6-diamino- (9CI) is a versatile compound with promising pharmacological properties and potential applications in the pharmaceutical industry.

Upstream product

• 124-41-4 sodium methylate 
• 506-93-4 guanidine nitrate 
• 105-34-0 methyl 2-cyanoacetate 
• 50-01-1 guanidine hydrochloride 
• 105-56-6 ethyl 2-cyanoacetate 
• 113-00-8 guanidine nitrate 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 55034-35-0 cyanoacetyl-guanidine 

Downstream Products

• 69205-79-4 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 40769-83-3 2-amino-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-one 
• 259145-29-4 2,6-diamino-5-(2-nitro-1-phenylethyl)-4(3H)-pyrimidinone 
• 637780-50-8 2,6-diamino-5-[2-nitro-1-(4-chlorophenyl)ethyl]-3H-pyrimidin-4-one 
• 637780-48-4 2,6-diamino-5-[2-nitro-1-(3-chlorophenyl)ethyl]-3H-pyrimidin-4-one 
• 637780-41-7 4-[1-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-nitroethyl]benzoic acid methyl ester 
• 259145-27-2 2,6-diamino-5-[1'-(nitromethyl)-3'-phenylpropyl]-4(3H)-pyrimidinone 
• 637780-46-2 2,6-diamino-5-[2-nitro-1-(2-chlorophenyl)ethyl]-3H-pyrimidin-4-one 
• 259145-26-1 4-[4-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-5-nitropentyl]benzoic acid methyl ester 
• 229470-22-8 4-[3-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-4-nitrobutyl]benzoic acid ethyl ester 
• 120040-42-8 2-amino-6-bromo-4(3H)-pyrido[2,3-d]pyrimidinone 

Relevant articles and documents

Synthesis and mycobacterial evaluation of 5-substituted-6-acetyl-2-amino-7-methyl-5,8-dihydropyrido-[2,3-d]pyrimidin-4(3H)-one derivatives

5-Substituted-6-acetyl-2-amino-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one derivatives were synthesized and evaluated against Mycobacterium tuberculosis H37Rv, Mycobacterium aurum, Escherichia coli, and Staphylococcus aureus as well as a human monocyte-derived macrophage (THP-1), and murine macrophage (RAW 264.7) cell lines to assess their antibacterial and cytotoxic potential, respectively. The compounds showed activity in the range of 1.95–125 μg/ml against M. tuberculosis but showed no activity against M. aurum, E. coli, and S. aureus, indicating selectivity towards slow-growing mycobacterial pathogens. The compounds exhibited very low to no cytotoxicity up to 500 μg/ml concentration against eukaryotic cell lines. The most potent molecule, 2l, showed a minimum inhibitory concentration of 1.95 μg/ml against M. tuberculosis H37Rv and a selectivity index of >250 against both the eukaryotic cell lines. Furthermore, 2l showed moderate inhibition of whole-cell mycobacterial drug-efflux pumps when compared to verapamil, a known potent inhibitor of efflux pumps. Thus, derivative 2l was identified as an antituberculosis hit molecule, which could be used to yield more potent lead molecules.

Green Microwave-assisted Multicomponent Route to the Formation of 5,8-Dihydropyrido[2,3-d]pyrimidine Skeleton in Aqueous Media

Three-component synthesis of 5-substituted 6-acetyl-2-amino-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidines was brought to facile energy-efficient and environmental-friendly conditions using multicomponent reaction, microwave field as an activation method and hot water as a solvent. A series of the target compounds was synthesized using the developed procedure.