43029-19-2

Basic information

• Product Name: 2-AMINO-3-HYDROXYPYRIMIDINE
• Synonyms: 2(1H)-Pyrazinone,3-amino-(9CI);2-Amino-3-hydroxypyrazine;3-Amino-2(1H)-pyrazinone;3-Amino-2-pyrazinol;3-AMinopyrazin-2(3H)-one;2-aMinopyriMidin-1(6H)-ol;3-AMinopyrazin-2(1H)-one;3-Amino-1H-pyrazin-2-one
• CAS NO: 43029-19-2
• Molecular Formula: C₄H₅N₃O
• Molecular Weight: 111.1
• Product Categories: VARIOUSAMINE
• Mol File: 43029-19-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 300-301℃
• Boiling Point: 538.9 °C at 760 mmHg
• Flash Point: 279.7 °C
• Appearance: /
• Density: 1.55
• Vapor Pressure: 3.14E-12mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.08±0.40(Predicted)
• CAS DataBase Reference: 2-AMINO-3-HYDROXYPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-HYDROXYPYRIMIDINE(43029-19-2)
• EPA Substance Registry System: 2-AMINO-3-HYDROXYPYRIMIDINE(43029-19-2)

Safety Data

• Hazardous Substances Data: 43029-19-2(Hazardous Substances Data)

Usage

Description

2-AMINO-3-HYDROXYPYRIMIDINE, also known as 2-amino-3-pyrimidinol, is an organic compound with the molecular formula C4H5N3O. It is a heterocyclic compound featuring a pyrimidine ring structure with an amino group at the 2nd position and a hydroxyl group at the 3rd position. 2-AMINO-3-HYDROXYPYRIMIDINE serves as an important intermediate in the synthesis of various biologically active molecules and pharmaceuticals due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-AMINO-3-HYDROXYPYRIMIDINE is used as a key intermediate in the synthesis of various 2(1H)-pyrazinones, which are known to act as inhibitors of protein kinases. These pyrazinones have potential applications in the development of drugs targeting various diseases, including cancer and inflammatory conditions, by modulating the activity of specific protein kinases involved in these pathological processes.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-AMINO-3-HYDROXYPYRIMIDINE is utilized as a building block for the design and development of novel therapeutic agents. Its unique chemical structure allows for the creation of diverse pyrimidine-based compounds with potential biological activities, making it a valuable tool for drug discovery and optimization efforts.
Used in Chemical Synthesis:
2-AMINO-3-HYDROXYPYRIMIDINE is also employed as a versatile synthetic building block in organic chemistry, particularly for the preparation of various pyrimidine-containing compounds. Its reactivity and functional groups enable the formation of a wide range of derivatives, which can be further modified and explored for their potential applications in various fields, such as materials science, agrochemistry, and pharmaceuticals.

InChI:InChI=1/C4H5N3O/c5-3-4(8)7-2-1-6-3/h1-2H,(H2,5,6)(H,7,8)

Upstream product

• 187973-44-0 3-(benzyloxy)-5-bromopyrazin-2-amine 
• 156331-25-8 2-amino-3-azidopyrazine 
• 55321-99-8 3-oxo-3,4-dihydropyrazine-2-carboxamide 

Downstream Products

• 931-18-0 1,4-dihydropyrazine-2,3-dione 
• 83831-20-3 C₃₀H₂₅N₃O₈ 
• 31613-87-3 3-aminopyrazine-2-thiol 

Relevant articles and documents

Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents

To explore the application potential of dual prodrug strategies in the development of anti-HCV agents, a variety of sofosbuvir derivatives with modifications at the C4 or N3 position of the uracil moiety were designed and synthesized. Some compounds exhibited potent anti-HCV activities, such as 4e and 8a–8c with similar EC50 values (0.20–0.22 μM) comparative to that of sofosbuvir (EC50 = 0.18 μM) in a genotype 1b based replicon Huh-7 cell line. Moreover, 8b displayed a good human plasma stability profile, and was easily metabolized in human liver microsomes expectantly. On the other hand, aiming to discover novel anti-HCV nucleosides, pyrazin-2(1H)-one nucleosides and their phosphoramidate prodrugs were investigated. Several active compounds were discovered, such as 25e (EC50 = 7.3 μM) and S-29b (EC50 = 19.5 μM). This kind of nucleosides were interesting and would open a new avenue for the development of antiviral agents.

Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library.

Synthesis of an N-aminopyrazinonium analogue of cytidine

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