156647-96-0

Basic information

• Product Name: 4-HYDROXY-6-METHYLPYRIMIDINE
• Synonyms: AKOS BC-0740;6-METHYL-4(3H)-PYRIMIDINONE;4-Pyrimidinol, 6-methyl- (9CI);2-Ethyl-6-methyl-3-pyridinol succinate;Mexidol Emicidine
• CAS NO: 156647-96-0
• Molecular Formula: C₅H₆N₂O
• Molecular Weight: 110.11
• EINECS: 222-543-4
• Product Categories: PYRIMIDINE
• Mol File: 156647-96-0.mol

Chemical Properties

• Boiling Point: 242.1℃
• Flash Point: 100.2℃
• Appearance: /
• Density: 1.215
• Vapor Pressure: 0.496mmHg at 25°C
• Refractive Index: 1.576
• PKA: 9.11±0.10(Predicted)
• CAS DataBase Reference: 4-HYDROXY-6-METHYLPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-6-METHYLPYRIMIDINE(156647-96-0)
• EPA Substance Registry System: 4-HYDROXY-6-METHYLPYRIMIDINE(156647-96-0)

Safety Data

• Hazardous Substances Data: 156647-96-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-6-METHYLPYRIMIDINE is used as a starting material for the production of various pharmaceuticals due to its unique chemical structure and reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Agricultural Chemical Industry:
In the agricultural sector, 4-HYDROXY-6-METHYLPYRIMIDINE is employed as a precursor in the synthesis of agricultural chemicals, such as pesticides and herbicides, leveraging its chemical properties to enhance crop protection and yield.
Used in Medicinal Chemistry Research:
4-HYDROXY-6-METHYLPYRIMIDINE is utilized as an important building block in medicinal chemistry, facilitating the design and synthesis of novel compounds with potential therapeutic effects, thus playing a crucial role in drug discovery and development.

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

Upstream product

• 56-04-2 6-methyl-2-thiouracil 
• 6328-58-1 4-Hydroxy-6-methyl-2-methylthiopyrimidine 
• 3473-63-0 formamidine acetic acid 
• 105-45-3 acetoacetic acid methyl ester 
• 21731-17-9 methyl 3-aminocrotonate 
• 71-36-3 butan-1-ol 
• 3524-87-6 6-methyl-3H-pyrimidin-4-one 

Downstream Products

• 3438-52-6 5-bromo-6-methylpyrimidin-4-ol 
• 1436405-35-4 N-((5-((4-(3-chloro-4-(pyridin-2-ylmethoxy)phenoxy)-6-methylpyrimidin-5-yl)ethynyl)furan-2-yl)methyl)-2-(methylsulfonyl)ethanamine 
• 1436405-34-3 4-(3-chloro-4-(pyridin-2-ylmethoxy)phenoxy)-5-ethynyl-6-methylpyrimidine 
• 1436405-33-2 4-(3-chloro-4-(pyridin-2-ylmethoxy)phenoxy)-5-iodo-6-methylpyrimidine 
• 1436405-31-0 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-ethynyl-6-methylpyrimidin-4-amine 
• 912353-90-3 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-methyl-5-((5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)ethynyl)pyrimidin-4-amine 
• 1436405-30-9 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-methyl-5-(2-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)vinyl)pyrimidin-4-amine 
• 1436405-28-5 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-methyl-5-vinylpyrimidin-4-amine 
• 912354-47-3 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-iodo-6-methylpyrimidin-4-amine 
• 1436405-29-6 N-(3-(-2-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-methylpyrimidin-5-yl)vinyl)phenyl)-4-(dimethylamino)but-2-enamide 
• 7752-74-1 5-iodo-6-methyl-3H-pyrimidin-4-one 
• 83410-15-5 4-chloro-5-iodo-6-methyl-pyrimidine 
• 7752-74-1 4-hydroxy-5-iodo-6-methylpyrimidine 

Relevant articles and documents

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-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.

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.

Scalable synthesis of 4-substituted 5-bromo-6-methylpyrimidines

Small halogenated heteroaromatic ring systems are valuable monomers, which can enable rapid access to novel and desirable chemical space, in part because of their ability to participate in established cross coupling chemistry such as the Heck, Stille, and Suzuki reactions. Described is a practical, scalable synthetic route towards the construction of a diverse array of 4-substituted 5-bromo-6-methylpyrimidine monomers. Georg Thieme Verlag Stuttgart · New York.

Unsymmetrical cyclic diamine compound

A cyclic diamine compound of formula (1): wherein A is (CH2)n, (CH2)n—CH═CH, CO—(CH2)n or CO—(CH2)n—CH═CH, in which n is a number of 0 to 3; Z represents a formula (2) or (3): in which R1, R2, R4, R5 and R6 are individually a hydrogen atom, alkyl group, alkoxy group, halogen atom or nitro group; R3 is a hydrogen atom, alkyl group, alkoxy group, halogen atom, nitro group, naphthyl group, or phenyl group which may be substituted by 1 to 3 substituents selected from the group consisting of alkyl groups, alkoxy groups, halogen atoms, a nitro group and a phenyl group; and X and Y are individually CH or a nitrogen atom; and m is 1 or 2; an acid-addition salt thereof, or a hydrate thereof, and a medicine containing such a compound.

Cyclic diamine compound with 6-membered ring groups

A cyclic diamine compound of formula (1): wherein A is a single bond or C≡C; X and Y are individually CH or a nitrogen atom; m is 1 or 2; and n is a number of 1 to 5; an acid-addition salt thereof, or a hydrate thereof. The compound has excellent inhibitory effects on both cell adhesion and cell infiltration and is useful as a medicine for prevention or treatment of diseases such as allergy, asthma, rheumatism, arteriosclerosis and inflammation.

Process for preparing 4-hydroxypyrimidine

A process for preparing a 4-hydroxypyrimidine of Formula III: STR1 wherein R1 and R2 each represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms or an aralkyl group having 2 to 10 carbon atoms, and R4 represents hydrogen an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, which comprises subjecting a 3-amino-2-unsaturated carboxylate of Formula I: STR2 wherein R1 and R2 are as defined above and R3 represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and a carboxylic acid amide of Formula II: wherein R4 is as defined above, to reaction with each other in the presence of a base.

TAUTOMERIC EQUILIBRIA OF 2(4)-MONOOXOPYRIMIDINES IN THE GAS PHASE, IN LOW-TEMPERATURE MATRICES AND IN SOLUTION

IR absorption spectra, including the NH, OH and C=O stretching regions, have been recorded for 4-oxo-6-methyl- and 2-oxo-4,6-dimethyl pyrimidines and several related derivatives, in the gas phase, in low-temperature inert matrices, and in several liquid solvents.All the 4-oxopyrimidines in the gas phase, and 4-oxo-6-methylpyrimidine in low-temperature matrices, exhibit comparable populations of the keto and enol forms.By contrast the 2-oxopyrimidines are predominantly in the enol forms.Both classes of compounds are predominantly in the keto form in liquid solvent systems.The tautomeric equilibrium constant (KT) in the vapour phase for 4-oxo-2,6-dimethylpyrimidine is about 2, and for the other 4-oxopyrimidines is about 1.For 4-oxo-6-methylpyrimidine, the equilibrium constant in inert matrices varies slightly with the activity of the matrix gas, with the keto tautomer favoured in the more active matrix.From the temperature-dependence of KT, the free energy difference between the two tautomeric forms of 4-oxo-6-methylpyrimidine in the vapour phase has been calculated.Heats of vaporization have also been calculated for the various compounds and related to their abilities to associate by hydrogen bonding in the condensed phase.The UV absorption spectra of some of the foregoing have also been recorded in the gas phase, but these were of only limited value in studies of tautomeric equilibria, as compared to the IR spectra.