5326-80-7

Basic information

• Product Name: 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• Synonyms: 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine;1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 6-methyl- (9CI);(6-methyl-1H-pyrazolo[4,3-e]pyrimidin-4-yl)amine;6-methyl-1H-pyrazolo[4,3-e]pyrimidin-4-amine;MFCD02008690
• CAS NO: 5326-80-7
• Molecular Formula: C₆H₇N₅
• Molecular Weight: 149.15328
• EINECS: 226-206-2
• Product Categories: PYRIMIDINE
• Mol File: 5326-80-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 291.5°Cat760mmHg
• Flash Point: 155°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: 1.776
• CAS DataBase Reference: 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine(5326-80-7)
• EPA Substance Registry System: 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine(5326-80-7)

Safety Data

• Hazardous Substances Data: 5326-80-7(Hazardous Substances Data)

Usage

Description

6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine is an organic compound belonging to the pyrazolo[3,4-d]pyrimidin class, characterized by a molecular formula of C8H8N6 and a molar mass of 176.19 g/mol. As a derivative of pyrazolo[3,4-d]pyrimidine, it features an amine group, making it a valuable building block in pharmaceutical research and development for the synthesis of various bioactive compounds, particularly in medicinal chemistry. Its unique structure and properties also lend it potential applications in organic synthesis and chemical biology.

Uses

Used in Pharmaceutical Research and Development:
6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine is utilized as a building block for the synthesis of bioactive compounds, playing a crucial role in the development of new pharmaceuticals. Its presence in the molecular structure can contribute to the desired biological activity and therapeutic effects of the resulting compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine is employed for its potential to enhance the properties of drug candidates. Its incorporation into molecular structures can improve pharmacokinetics, potency, and selectivity, leading to more effective and safer medications.
Used in Organic Synthesis:
6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine is also used in organic synthesis, where its unique structure allows for the creation of a variety of complex organic molecules. This can be particularly useful in the development of novel compounds with specific functions or properties.
Used in Chemical Biology:
Due to its distinctive structural features, 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine finds applications in chemical biology, where it can be used to study biological processes or to develop new tools for biological research, such as probes or inhibitors targeting specific biological pathways or enzymes.

InChI:InChI=1/C6H7N5/c1-3-9-5(7)4-2-8-11-6(4)10-3/h2H,1H3,(H3,7,8,9,10,11)

Upstream product

• 67-56-1 methanol 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 
• 124-42-5 acetamidine hydrochloride 
• 16617-46-2 3-amino-4-cyano-2H-pyrazole 
• 16617-46-2 3-Amino-4-cyanopyrazole 
• 75-05-8 acetonitrile 
• 117868-30-1 N-(4-cyano-1⁽²⁾H-pyrazol-3-yl)-acetamide 
• 30129-57-8 NSC 76237 
• 30129-53-4 4-chloro-6-methylpyrazolo<3,4-d>pyrimidine 

Downstream Products

• 1075736-81-0 1-{[3-(4-amino-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl]carbonyl}-D-prolinamide 
• 1075736-82-1 phenylmethyl 3-(4-amino-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzoate 
• 936758-10-0 1-(2,4-difluorophenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 936758-08-6 1-(2-fluorophenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 7154-45-2 4-amino-3-methyl-N¹-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 936758-09-7 1-(4-fluorophenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1075736-85-4 1-{[3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl]carbonyl}-D-prolinamide 
• 1075736-86-5 N-[(1R)-2-amino-1-methyl-2-oxoethyl]-3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzamide 
• 1075736-87-6 N-(2-amino-2-oxoethyl)-3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzamide 
• 1075736-83-2 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzoic acid 

Relevant articles and documents

Regioselective Synthesis of Pyrazolo[3,4-D[Pyrimidine Based Carbocyclic Nucleosides as Possible Antiviral Agent

Carbocyclic nucleosides are considered as nucleoside mimetic having high therapeutic potentials, however diverse exploration is still limited due to their synthetic difficulties. The major challenges are associated with the preparation of new base and carbocyclic sugar key intermediates. The modified base may provide conformational advantage to achieve better nucleoside mimetics and may also help in increasing the drug-like properties. In this manuscript, we report the use of acetamidine hydrochloride to synthesize 6-methyl-4-amino-pyrazolo[3,4-d]pyrimidine base and regioselective synthesis of six new carbocyclic nucleosides (6a-f) for antiviral evaluation. Theoretical investigations were carried out on the basis of thermodynamic and kinetic stability using MM based energy optimizations and QM based transition state search for the significant regioselectivity, which was further experimentally analyzed by NOE and UV spectroscopy.

1-PHENYLPYRROLIDIN-2-ONE DERIVATIVES AS PERK INHIBITORS

The invention is directed to substituted pyrrolidinone and imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I: (I) wherein R1, R2, R3, R4, R5, R6, R7, X and Y are as defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases/injuries associated with activated unfolded protein response pathways, such as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson's disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt- Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

PYRAZOLO-PYRIMIDINE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS

The present invention is directed to compounds of formula (I): a process for their preparation, to pharmaceutical compositions comprising the compounds and the preparation of said compositions, to intermediates and to use of the compounds for the manufacture of a medicament for therapeutic treatment, particularly for the treatment of inflammation and/or allergic conditions.