5444-02-0

Basic information

• Product Name: 3-Cyano-2,6-dihydroxy-4-methylpyridine
• Synonyms: 1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitril;2,6-DIHYDROXY-4-METHYL-3-PYRIDINECARBONITRILE;2,6-DIHYDROXY-3-CYANO-4-METHYLPYRIDINE;2,6-DIHYDROXY-4-METHYLNICOTINONITRILE;2,6-DIHYDROXY-4-METHYLPYRIDINE-3-CARBONITRILE;3-CYANO-2,6-DIHYDROXY-4-METHYLPYRIDINE;1,2-dihydro-6-hydroxy-4-methyl-2-oxonicotinonitrile;2,6-Dihydroxy-4-methyl-3-piridinecarbonitrile
• CAS NO: 5444-02-0
• Molecular Formula: C₇H₆N₂O₂
• Molecular Weight: 150.13
• EINECS: 226-639-7
• Product Categories: Intermediates of Dyes and Pigments;Heterocyclic Compounds;Pyridines;Alcohols;Monomers;Polymer Science;alcohol|cyanide
• Mol File: 5444-02-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 315 °C (dec.)(lit.)
• Boiling Point: 323 °C at 760 mmHg
• Flash Point: 149.1 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: 1.491
• PKA: 3.59±0.58(Predicted)
• CAS DataBase Reference: 3-Cyano-2,6-dihydroxy-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyano-2,6-dihydroxy-4-methylpyridine(5444-02-0)
• EPA Substance Registry System: 3-Cyano-2,6-dihydroxy-4-methylpyridine(5444-02-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5444-02-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow solid

Uses

3-Cyano-2,6-dihydroxy-4-methylpyridine is a synthetic human uridine phosphorylase-1 inhibitor, reduces HepG2 cell proliferation through cell cycle arrest and senescenceis and is used in the synthesis of disperse dyes. Also used in the synthesis of mGluR5 non-competitive antagonists.

InChI:InChI=1/C9H15NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-5H,6-7H2,1-3H3

Upstream product

• 110-89-4 piperidine 
• 107-91-5 cyanoacetimide 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 107-91-5 cyanoacetic acid amide 
• 96-34-4 methyl chloroacetate 
• 105-34-0 methyl 2-cyanoacetate 
• 55212-82-3 ethyl 3-morpholinocrotonate 
• 66003-96-1 β-morpholinoethylcrotonate 
• 73018-20-9 3-oxobutanoic acid 
• 105143-58-6 piperidinium 3-cyano-1,6-dihydro-4-methyl-6-oxo-2-pyridinolate 
• 93272-85-6 3-cyano-6-hydroxy-4-methyl-2(1H)-pyridinethione 
• 105143-58-6 2,6-dihydroxy-3-cyano-4-methylpyridine piperidine salt 
• 5977-14-0 acetoacetamido 

Downstream Products

• 4664-16-8 4-methyl-2,6-dihydroxypyridine 
• 26345-14-2 3-cyano-2,6-dimethoxy-4-methylpyridine 
• 815618-77-0 5-bromo-2,6-dihydroxy-4-methylnicotinonitrile 
• 38824-75-8 2,6-dibromo-4-methylpyridine-3-carbonitrile 
• 38841-54-2 2,6-dichloro-4-methyl-3-pyridinecarboxamide 
• 129432-25-3 2,6-dichloro-3-amino-4-methylpyridine 
• 51560-72-6 2,6-bis-(3'-methoxy-n-propylamino)-3-cyano-4-methylpyridine 
• 56331-52-3 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine 
• 243469-65-0 6-chloro-2-methoxy-4-methylnicotinonitrile 
• 796874-78-7 C₁₃H₉BrN₄O₂ 

Relevant articles and documents

Continuous flow synthesis of some 6- And 1,6-substituted 3-cyano-4-methyl-2-pyridones

In this study, six 6- and 1,6-substituted-3-cyano-4-methyl-2-pyri-dones were synthesized in a continuous flow microreactor system. The syntheses were realized at room temperature and the obtained results were compared to those achieved within classical syntheses. In order to optimize the continuous flow syntheses and increase the yield of the products, the retention time in the microreactor was varied by changing the flow rates of the reactant solutions. Furthermore, the reaction was optimized for 3-cyano-4,6-dimethyl-2-pyridone and 3-cyano-6-hydroxy-4-methyl-2-pyridone, which are comercially important in the pharmaceutical and dye industries. Both 2-pyridones were obtained in satisfactory yield of circa 60 % in less than 10 min. The resulting compounds were characterized by their melting points, FT-IR, 1H-NMR and UV–Vis spectra. The efficiency of the presented method for the synthesis of 2-pyridone-based molecules has promising potential for industrial production.

NEK6 KINASE INHIBITORS USEFUL FOR THE TREATMENT OF SOLID TUMORS

The mitotic kinases regulating the dynamics of centrosomes and the functions of the mitotic spindle are potential targets for the antitumour therapy. In the present invention some molecules with inhibitory activity on NEK6 have been identified. The present invention relates to such molecules and to the compositions including them for use as inhibitors of NEK6 in a method of treatment of tumours both in monotherapy and in combinations with other drugs.

Preparation method for nevirapine intermediate

The invention provides a preparation method for a nevirapine intermediate. The preparation method comprises: performing a cyclization reaction of ammonia water, methyl cyanoacetate and methyl acetoacetate to form a compound hydroxyl: 2,6-dihydroxy-3-cyano-4-methylpyridine; adding triethylamine dropwise, introducing chlorine gas at the temperature until the reaction is complete, and obtaining 2,6-dichloro-3-cyano-4-methylpyridine; adding concentrated sulfuric acid, heating to 120 DEG C to react for 3-5 h, and then cooling to 60 DEG C; adding water to perform hydrolysis reaction, and obtaining 2,6-dichloro-3-amido-4-methylpyridine; adding a degradation reagent sodium hypochlorite, and obtaining a nevirapine intermediate 2,6-dichloro-3-amino-4- methylpyridine by Hofmann reaction. According tothe preparation method, commonly used phosphorus oxychloride is replaced with the directly introduced chlorine gas, which solves the problems that the wastewater content is too high, it is difficultto perform treatment and the odor of phosphorus oxychloride is bad, and the one-time yield of the product is 90.1%.