5604-46-6

Basic information

• Product Name: 2-Amino-4,6-dichloro-5-formylpyrimidine
• Synonyms: 2-AMINO-4,6-DICHLORO-PYRIMIDINE-5-CARBALDEHYDE;2-AMINO-4,6-DICHLOROPYRIMIDINE-5-CARBOXALDEHYDE;2-AMINO-4,6-DICHLORO-5-FORMYL-PYRIMIDINE;2-AMINO-4,6-DICHLORO-5-PYRIMIDINECARBALDEHYDE;5-PYRIMIDINECARBOXALDEHYDE, 2-AMINO-4,6-DICHLORO-;2-AMINO-4,6-DICHLOROPYRIMIDINE-5-CARBOX&;2-amino-4,6-dichloro-5-pyrimid;2-azanyl-4,6-dichloro-pyrimidine-5-carbaldehyde
• CAS NO: 5604-46-6
• Molecular Formula: C₅H₃Cl₂N₃O
• Molecular Weight: 192
• EINECS: 1806241-263-5
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Aldehydes;Pyrazines, Pyrimidines & Pyridazines;Pyrimidine;Heterocycle intermediates;Pyrimidines;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrimidinesHeterocyclic Building Blocks;Building Blocks;C1 to C6;C4 to C5;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 5604-46-6.mol

Chemical Properties

• Melting Point: 208-224 °C
• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 202.7 °C
• Appearance: yellow solid
• Density: 1.688 g/cm³
• Vapor Pressure: 5.52E-07mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: 2-8°C
• PKA: -1.57±0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-Amino-4,6-dichloro-5-formylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4,6-dichloro-5-formylpyrimidine(5604-46-6)
• EPA Substance Registry System: 2-Amino-4,6-dichloro-5-formylpyrimidine(5604-46-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5604-46-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4,6-dichloro-5-formylpyrimidine is used as a substrate for the synthesis of an N-terminal surrogate in amino acid and peptide analogues. This application is significant because it allows for the creation of new and potentially beneficial pharmaceutical compounds, which can be used in the development of drugs for various medical conditions.
Used in Biochemical Research:
In the field of biochemistry, 2-Amino-4,6-dichloro-5-formylpyrimidine serves as a valuable substrate for the synthesis of various peptide and amino acid analogues. This enables researchers to study the structure, function, and interactions of these analogues, which can lead to a better understanding of biological processes and the development of novel therapeutic strategies.
Used in Chemical Synthesis:
2-Amino-4,6-dichloro-5-formylpyrimidine is also utilized in chemical synthesis, particularly for the production of complex organic molecules. Its unique structure and functional groups make it a versatile building block for the creation of a wide range of compounds with diverse applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C5H3Cl2N3O/c6-3-2(1-11)4(7)10-5(8)9-3/h1H,(H2,8,9,10)

Upstream product

• 56-09-7 2-amino-6-hydroxy-pyrimidin-4(3H)-one 
• 68-12-2 N,N-dimethyl-formamide 
• 56-09-7 2-aminopyrimidine-4,6-diol 
• 56-05-3 2-Amino-4,6-dichloropyrimidine 

Downstream Products

• 155087-32-4 2-amino-4-chloro-6-(N-ethyl-N-phenylamino)pyrimidine-5-carbaldehyde 
• 85840-19-3 2-amino-4-chloro-6-<(4-phenylbutyl)amino>-5-pyrimidinecarboxaldehyde 
• 141019-46-7 diethyl N-<4-<4-<(2-amino-6-chloro-5-formylpyrimidin-4-yl)amino>butyl>benzoyl>-L-glutamate 
• 141019-39-8 diethyl N-<4-<4-<(2-amino-6-chloro-5-formylpyrimidin-4-yl)amino>-1-butynyl>benzoyl>-L-glutamate 
• 155087-30-2 2-Amino-4-chloro-6-diethylamino-pyrimidine-5-carbaldehyde 
• 155087-31-3 2-Amino-4-chloro-6-phenylamino-pyrimidine-5-carbaldehyde 
• 142979-46-2 2-amino-6-[benzyl(methyl)amino]-4-chloropyrimidine-5-carbaldehyde 
• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 
• 177483-58-8 2-amino-6-(N-benzyl-but-3-enylamino)-4-chloro-5-formylpyrimidine 
• 178392-67-1 2-amino-6-(N-benzyl-N-3-butynylamino)-4-chloro-5-formylpyrimidine 
• 220545-79-9 2-amino-6-(N-3-butynylamino-N-4-methoxybenzyl)-4-chloro-5-formylpyrimidine 
• 244288-51-5 2-amino-4-chloro-6-di(4-methoxybenzyl)-amino-5-pyrimidine carbaldehyde 
• 850554-81-3 2-amino-4,6-dichloro-5-hydroxymethylpyrimidine 
• 377727-26-9 SCH 412348 

Relevant articles and documents

Nitrogen-containing fused tricyclic derivative and application thereof

The invention discloses a nitrogen-containing fused tricyclic derivative and application thereof, and particularly relates to a novel nitrogen-containing fused tricyclic derivative and a pharmaceutical composition containing the nitrogen-containing fused tricyclic derivative, and the nitrogen-containing fused tricyclic derivative can be used as a selective adenosine A2A receptor antagonist. The invention also relates to a method for preparing the compound and the pharmaceutical composition and application of the compound and the pharmaceutical composition in preparation of drugs for treating adenosine A2A receptor related diseases, especially Parkinson's disease.

Nitrogen-containing fused tricyclic derivatives and application thereof

The invention discloses a nitrogen-containing fused tricyclic derivative and application thereof, and particularly relates to a novel nitrogen-containing fused tricyclic derivative and a pharmaceutical composition containing the nitrogen-containing fused tricyclic derivative, and the nitrogen-containing fused tricyclic derivative can be used as a selective adenosine A2A receptor antagonist. The invention also relates to a method for preparing the compound and the pharmaceutical composition and application of the compound and the pharmaceutical composition in preparation of drugs for treating adenosine A2A receptor related diseases, especially Parkinson's disease.

Development of pyrazolo[3,4-d]pyrimidine-6-amine-based TRAP1 inhibitors that demonstrate in vivo anticancer activity in mouse xenograft models

TNF Receptor Associated Protein 1 (TRAP1) is a mitochondrial paralog of Hsp90 related to the promotion of tumorigenesis in various cancers via maintaining mitochondrial integrity, reducing the production of reactive oxygen species, and reprogramming cellular metabolism. Consequently, Hsp90 and TRAP1 have been targeted to develop cancer therapeutics. Herein, we report a series of pyrazolo[3,4-d]pyrimidine derivatives that are mitochondria-permeable TRAP1 inhibitors. Structure-based drug design guided the optimization of potency, leading to the identification of compounds 47 and 48 as potent TRAP1 and Hsp90 inhibitors with good metabolic and plasma stability as well as acceptable CYP and hERG inhibition. X-ray co-crystallization studies confirmed both 47 and 48 interact with the ATP binding pocket in the TRAP1 protein. Compounds 47 and 48 demonstrated excellent anticancer efficiency in various cancer cells, with limited toxicity over normal hepatocyte and prostate cells. Mouse PC3 xenograft studies showed 47 and 48 significantly reduced tumor growth.

Application of five-membered heterocycle pyrimidine compound

The invention belongs to the field of medicine and particularly relates to application of a five-membered heterocycle pyrimidine compound with the structural features as shown in formula (I) and the pharmaceutically acceptable salt of the five-membered heterocycle pyrimidine compound serving as nucleotide oxidative damage repairase MTH1 inhibitors. Pharmacological experiment results show that thecompound can evidently inhibit the activity of MTH1 and can be used for preventing and treating clinical diseases related to MTH1.

Fluorinated adenosine A2A receptor antagonists inspired by preladenant as potential cancer immunotherapeutics

Antagonism of the adenosine A2A receptor on T cells blocks the hypoxia-adenosinergic pathway to promote tumor rejection. Using an in vivo immunoassay based on the Concanavalin A mouse model, a series of A2A antagonists were studied and identified preladenant as a potent lead compound for development.Molecular modeling was employed to assist drug design and subsequent synthesis of analogs and those of tozadenant, including fluorinated polyethylene glycol PEGylated derivatives. The efficacy of the analogs was evaluated using two in vitro functional bioassays, and compound 29, a fluorinated triethylene glycol derivative of preladenant, was confirmed as a potential immunotherapeutic agent.

nitrogen hybridization guanine nucleoside and its synthetic method and the use of DNA sequencing

The invention discloses hybrid azaguanosine as well as a synthesis method and an application thereof in DNA sequencing. The synthesis method comprises the steps: removing a protecting group of a compound as shown in formula (III) in the specification under an alkaline condition to obtain a compound as shown in formula (II) in the specification; further demethylating to obtain a compound as shown in formula (I) in the specification, i.e. 7-deaza-7-halogen-8-aza-guanosine, wherein R1 is H or OH, R2 is I, Br or Cl, and R3 is H or a compound shown in the specification. The hybrid azaguanosine disclosed by the invention is a novel reagent for DNA sequencing, which, compared to guanosine failing to substitute nitrogen on 8 sites, is more excellent in base identifying effect and more stable in DNA chain structure. Meanwhile, different from the prior art that 8-site nitrogen-substituted guanosine is complex in synthesis method, low in yield and unsuitable for commercial production, the synthesis method disclosed by the invention is easily available in raw material required, and adopts conventional chemical synthesis reaction; and the method is relatively high in yield, and suitable for wide popularization and application.

HETEROCYCLIC GTP CYCLOHYDROLASE 1 INHIBITORS FOR THE TREATMENT OF PAIN

The present invention relates to the field of small molecule heterocyclic inhibitors of GTP cyclohydrolase (GCH-I), or a tautomer, prodrug, or pharmaceutically acceptable salt thereof. The invention also features pharmaceutical compositions of the compounds and the medical use of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, or neuropathic pain).

Synthesis of novel 2-cyano-7-deaza-8-azapurine- and 2-cyano-8-azapurine- derived nucleosides

A novel systematic approach to the synthesis of 2-cyano-7-deaza-8-azapurine derived nucleosides is described. It is shown how this chemistry was developed with the labile 2-substituted nitrile position in mind, and also how the same approach is applicable to 2-cyano-8-azapurine derived nucleosides.

5-6-BICYCLIC HETEROAROMATIC COMPOUNDS WITH ANTIBACTERIAL ACTIVITY

Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

Aminopyrimidine-based donor-acceptor chromophores: Push-pull versus aromatic behaviour

Novel 2-aminopyrimidines substituted with two electron-donor dialkylamino groups and either one dicyanovinyl (4a-d) or one tricyanovinyl (7a-d) electron-acceptor group have been synthesized, and the balance between their push-pull character and their aromatic behaviour has been studied by experimental (spectroscopic, electrochemical and X-ray analysis) and theoretical (DFT/B3LYP/6-31G* *) methods. Calculations reveal that the push-pull character is energetically favoured with respect to the preservation of the aromaticity of the pyrimidine ring. X-ray analysis of 7a confirms the theoretical predictions and reveals a strong distortion from planarity due to the steric interaction between the tricyanovinyl group and the adjacent dialkylamino moieties. In contrast with what would normally be expected for push-pull compounds, the visible-region absorption bands of 4a-d and 7a-d are associated with π-π* electronic transitions and not with intramolecular charge-transfer absorptions. In each compound, both the HOMO and the LUMO are spread over the whole molecule and are not located on the donor and acceptor moieties, respectively, as is the case for typical push-pull chromophores. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.