3524-87-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-6-methylpyrimidine is used as a key intermediate in the synthesis of various antitumor compounds. It plays a crucial role in the preparation of adenine-based antitumor agents, which are designed to target and inhibit the growth of cancer cells.
Additionally, 4-Hydroxy-6-methylpyrimidine is utilized in the synthesis of novel purine derivatives, which have potential applications as tyrosine kinase inhibitors. Tyrosine kinases are enzymes that play a significant role in cell signaling and are often overactive in cancer cells, leading to uncontrolled cell growth. Inhibiting these enzymes can help in the development of targeted cancer therapies.
Used in Chemical Industry:
In the chemical industry, 4-Hydroxy-6-methylpyrimidine is employed as a building block for the synthesis of various heterocyclic compounds, such as 3-cyanopyridine and m-amino-N-phenylbenzamide derivatives. These compounds have potential applications in the development of new drugs and materials with diverse properties and functions.

InChI:InChI=1/C5H6N2O/c1-4-2-5(8)7-3-6-4/h2-3H,1H3,(H,6,7,8)

Upstream product

• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 56-04-2 6-methyl-2-thiouracil 
• 53907-67-8 N-(3-methyl-isoxazol-5-yl)-formamide 
• 6328-58-1 6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one 
• 37893-08-6 2-hydrazino-6-methylpyrimidin-4(3H)-one 
• 17759-11-4 4-benzyloxy-6-methylpyrimidine 1-oxide 
• 109113-86-2 3-Formylamino-3-methyl-N-acetylacrylamide 
• 89991-24-2 2-(6-Methyl-pyrimidin-4-ylsulfanyl)-1-p-tolyl-ethanone 
• 89991-22-0 1-(4-Chloro-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 89991-23-1 1-(4-Bromo-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 89991-25-3 1-(4-Methoxy-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 3524-87-6 4-hydroxy-6-methylpyrimidine 
• 6328-58-1 4-Hydroxy-6-methyl-2-methylthiopyrimidine 
• 64-17-5 ethanol 

Downstream Products

• 17758-19-9 3,6-dimethylpyrimidin-4(3H)-one 
• 5541-07-1 4-methoxy-6-methylpyrimidine 
• 74519-13-4 4-oxo-1,6-dimethylpyrimidine 
• 51793-97-6 6-methylpyrimidine-4(3H)-thione 
• 7752-74-1 5-iodo-6-methyl-3H-pyrimidin-4-one 
• 83942-10-3 4,5-dichloro-6-methyl-pyrimidine 
• 3524-87-6 4-hydroxy-6-methylpyrimidine 
• 89991-27-5 2-(6-methyl-4-pyrimidinylthio)-cyclohexanone 
• 89991-26-4 ω-(6-methyl-4-pyrimidinylthio)-acetophenone 
• 89991-24-2 2-(6-Methyl-pyrimidin-4-ylsulfanyl)-1-p-tolyl-ethanone 
• 89991-22-0 1-(4-Chloro-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 89991-23-1 1-(4-Bromo-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 89991-25-3 1-(4-Methoxy-phenyl)-2-(6-methyl-pyrimidin-4-ylsulfanyl)-ethanone 
• 14027-64-6 1.3.6-Trimethyl-4-oxo-1H.4H-pyrimidinium-iodid 

Relevant academic research and scientific papers

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones

A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity. The benign protocol offers a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.

Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values 1 μM for EGFR and 5 μM for A-549 and HL60 cells growth inhibition.

5-Alkynyl-pyridines

This invention relates to 5-alkynyl-pyridine of general formula (I) their use as inhibitors of the activity of PI3Kalpha, pharmaceutical compositions containing them, and their use as a medicaments for the treatment and/or prevention of diseases characterized by excessive or abnormal cell proliferation and associated conditions such as cancer. The groups R1 to R6 and n have the meanings given in the claims and in the specification

NEW 5-ALKYNYL-PYRIDINES

5-alkynyl-pyridine of general formula (I) which are inhibitors of the activity of PI3K alpha, and their use in the treatment of diseases characterized by excessive or abnormal cell proliferation, such as cancer.

5-ALKYNYL-PYRIMIDINES

The present invention encompasses compounds of general formula (1) wherein R1 to R4 R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.

NEW 5-ALKYNYL-PYRIDINES

This invention relates to 5-alkynyl-pyridine of general formula (I) their use as inhibitors of the activity of PI3Kalpha, pharmaceutical compositions containing them, and their use as a medicaments for the treatment and/or prevention of diseases characterized by excessive or abnormal cell proliferation and associated conditions such as cancer. The groups R1 to R6 and n have the meanings given in the claims and in the specification.

NEW 5-ALKYNYL-PYRIDINES

This invention relates to 5-alkynyl-pyridine of general formula (I) their use as inhibitors of the activity of P13Kalpha, pharmaceutical compositions containing them, and their use as a medicaments for the treatment and/or prevention of diseases characterized by excessive or abnormal cell proliferation and associated conditions such as cancer. The groups R1 to R6 and n have the meanings given in the claims and in the specification.

5-ALKYNYL-PYRIMIDINES

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.

Synthesis and evaluation of novel pyrimidine-based dual EGFR/Her-2 inhibitors

A structure-activity relationship study of 4-anilinopyrimidines for dual EGFR/Her-2 inhibitor has resulted in the identification of 4-anilino-5-alkenyl or 5-alkynyl-6-methylpyrimidine derivatives that have exhibited effective inhibitory activity against both enzymes. The presence of 5-alkenyl or 5-alkynyl moiety bearing terminal hydrophilic group played important role for inhibition of these enzymes. Selected compounds in the series demonstrated some activity against Her-2 dependent cell line (BT474).

A method for the reductive scission of heterocyclic thioethers

A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants which are not compatible with the standard Raney nickel conditions such as sulfides, sulfones, and thiophenes. In addition, benzyl esters, benzyl amides, and benzyl carbamates are tolerated by the reductive reaction conditions.