100643-27-4

Basic information

• Product Name: 4-Pyrimidinol, 2,6-diamino- (9CI)
• Synonyms: 4-Pyrimidinol, 2,6-diamino- (9CI);2,4-diaMino-6(1H)-pyriMidone
• CAS NO: 100643-27-4
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.11664
• Product Categories: PYRIMIDINE;Pyrimidines
• Mol File: 100643-27-4.mol

Chemical Properties

• Boiling Point: 288.5 °C at 760 mmHg
• Flash Point: 128.3 °C
• Appearance: /
• Density: 1.84 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.85±0.10(Predicted)
• CAS DataBase Reference: 4-Pyrimidinol, 2,6-diamino- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyrimidinol, 2,6-diamino- (9CI)(100643-27-4)
• EPA Substance Registry System: 4-Pyrimidinol, 2,6-diamino- (9CI)(100643-27-4)

Safety Data

• Hazardous Substances Data: 100643-27-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Pyrimidinol, 2,6-diamino(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds for [application reason]. Its unique chemical structure and properties allow it to be a versatile building block in the creation of new drugs and therapies.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-Pyrimidinol, 2,6-diamino(9CI) is utilized as a subject of study for understanding its chemical properties and exploring its potential applications in drug development. Its structure makes it a promising candidate for further research to enhance the discovery of novel therapeutic agents.

Upstream product

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

Downstream Products

• 651358-53-1 2-amino-4-oxo-6-(3,4,5-trimethoxybenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-52-0 2-amino-4-oxo-6-(4-phenylbenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-49-5 2-amino-4-oxo-6-(3,4-dichlorobenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-48-4 2-amino-6-(2,4-dichlorobenzyl)-3,7-dihydro-4H-pyrrolo-[2,3-d]pyrimidin-4-one 
• 651358-45-1 2-amino-4-oxo-6-(2-chlorobenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-44-0 2-amino-6-(2-methylbenzyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 651358-47-3 2-amino-4-oxo-6-(2,5-dimethoxybenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-46-2 2-amino-4-oxo-6-(4-chlorobenzyl)-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 651358-43-9 2-amino-4-oxo-6-benzyl-3,7-dihydropyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

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.

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.

Preparation methods of 2,4-diamido-5-nitroso-6-hydroxypyridine and guanine

The invention discloses a preparation method of 2,4-diamido-5-nitroso-6-hydroxypyridine. The preparation method comprises the following steps: (1) in a sodium methoxide methanol solution, carrying outa ring-closure reaction between methyl cyanoacetate and guanidine salt; (2) adding recycled absolute methanol to be diluted, filtering and recycling byproduct sodium nitrate; (3) concentrating a filter liquor, and recycling absolute methanol; (4) adding water to destroy excessive sodium methoxide, concentrating and recycling water-containing methyl alcohol; (5) in a diluted methane acid solution,carrying out a nitrosation reaction among an obtained concentrate, sodium nitrite and a nitrosation mother liquor; (6) after the reaction ends, carrying out cooling crystallization, filtering, takinga filter liquor as the nitrosation mother liquor to be used indiscriminately, and drying an obtained filter cake to obtain the 2,4-diamido-5-nitroso-6-hydroxypyridine. According to the preparation method, indiscriminate use of the nitrosation mother liquor and recycling of sodium nitrate and methyl alcohol are realized, and simultaneously the diluted methane acid solution is used for replacing concentrated sulfuric acid used, in the prior art, to carry out the nitrosation reaction, so that the recycling of a solvent and a reagent is facilitated, and the displacement of waste water is reduced.

Microwave-expedited one-pot, two-component, solvent-free synthesis of functionalized pyrimidines

The synthesis of a series of diversely substituted pyrimidines under solvent-free conditions in good yields is described. Under microwave irradiation, a variety of nucleophilic substrates containing the N?C?N unit with ?-dicarbonyl compounds, ethyl cyanoacetate, malononitrile, and chalcones was cyclized to give pyrimidines. A combinatorial type approach for a one-step synthesis has been developed where a ring-closing condensation is followed by spontaneous aromatization to afford 28 functionalized and aryl/alkyl substituted pyrimidines. CSIRO 2007.