64038-03-5

Basic information

• Product Name: 1,4,6-TRIMETHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE
• Synonyms: 1,2-dihydro-2-oxo-1,4,6-trimethyl-nicotinonitril;1,4,6-TRIMETHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE;1,2-Dihydro-1,4,6-trimethyl-2-oxopyridine-3-carbonitrile;1,2-Dihydro-2-oxo-1,4,6-trimethylnicotinonitrile;1,4,6-trimethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile(SALTDATA: FREE)
• CAS NO: 64038-03-5
• Molecular Formula: C9H10N2O
• Molecular Weight: 162.19
• Mol File: 64038-03-5.mol

Chemical Properties

• Melting Point: 202-204°
• Boiling Point: 306.3°Cat760mmHg
• Flash Point: 139°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0.000779mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: 1,4,6-TRIMETHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,6-TRIMETHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE(64038-03-5)
• EPA Substance Registry System: 1,4,6-TRIMETHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE(64038-03-5)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 64038-03-5(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C9H10N2O/c1-6-4-7(2)11(3)9(12)8(6)5-10/h4H,1-3H3

Upstream product

• 123-54-6 acetylacetone 
• 6330-25-2 N-methyl-2-cyanoacetamide 
• 110-89-4 piperidine 
• 87718-98-7 N-methyl cyanoacetamide 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 769-28-8 3-Cyano-4,6-dimethyl-2(1H)-pyridon 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 769-28-8 2-hydroxy-4,6-dimethyl-3-carbonitrile 
• 74-88-4 methyl iodide 
• 4108-63-8 1,4,6,6-tetramethyl-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carbonitrile 

Downstream Products

• 24667-08-1 1,4,6-trimethyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 

Relevant articles and documents

The Importance of Being Me: Magic Methyls, Methyltransferase Inhibitors, and the Discovery of Tazemetostat

Posttranslational methylation of histones plays a critical role in gene regulation. Misregulation of histone methylation can lead to oncogenic transformation. Enhancer of Zeste homologue 2 (EZH2) methylates histone 3 at lysine 27 (H3K27) and abnormal methylation of this site is found in many cancers. Tazemetostat, an EHZ2 inhibitor in clinical development, has shown activity in both preclinical models of cancer as well as in patients with lymphoma or INI1-deficient solid tumors. Herein we report the structure-activity relationships from identification of an initial hit in a high-throughput screen through selection of tazemetostat for clinical development. The importance of several methyl groups to the potency of the inhibitors is highlighted as well as the importance of balancing pharmacokinetic properties with potency.

Synthesis and reactions of 3-cyano-4,6-dimethyl-2-pyridone

Rapid synthesis of 3-cyano-4,6-dimethyl-2-pyridone 3, using piprazine as a catalyst was reported. X-ray data of the 4,6-dimethyl-2-oxo-1,2-dihydropyridine- 3-carbonitrile exhibited its oxo form. Synthesis of isoquinolinecarbonitrile and pyridylpyridazine using compound 3 was investigated. Reactivity of the synthesized pyridone toward different organic reagents was also studied.

Ionic liquid catalyzed 4,6-disubstituted-3-cyano-2-pyridone synthesis under solvent-free conditions

A green protocol for the synthesis of 4,6-disubstituted-3-cyano-2-pyridones from cyanoacetamides and 1,3-dicarbonyl compounds or chalcones using guanidine based ionic liquid as catalyst has been developed. In solvent-free conditions at 30 °C, [TMG][Lac] (1,1,3,3-tetramethylguanidine lactate) was found to have the highest catalytic activity among the ionic liquids including [TMG][Ac] (1,1,3,3-tetramethylguanidine acetate), [TMG][Pr] (1,1,3,3-tetramethylguanidine propionate), [TMG][n-Bu] (1,1,3,3-tetramethylguanidine n-butyrate) and [TMG][TFA] (1,1,3,3-tetramethylguanidine trifluoroacetate). The catalyst was recovered and recycled several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis of N-substituted 4,6-dimethyl-3-cyano-2-pyridones under microwave irradiation

N-substituted 4,6-dimethyl-3-cyano-2-pyridones have been prepared from acetylacetone, N-substituted cyanoacetamide, and pyperidine as catalyst under microwave irradiation without solvent. The rapid and simple method produced pure products in high yields. Copyright Taylor & Francis LLC.

Synthesis of substituted 3-cyano-2-pyridones: Part IV - Influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed synthesis of substituted 3-cyano-2-pyridones

Lipase from Candida rugosa has been used to study the influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed reaction of pyridone ring formation in water at 40°C. Starting with 1,3-diketones and cyanoacetamides and for comparison, the expected corresponding substituted 3-cyano-2-pyridones have been synthesized by chemical methods. Bulkier substitueras lower the initial reaction rate of the enzyme catalyzed reactions and consequently the yield of the corresponding pyridones. N-alkyl cyanoacetamides are more reactive in comparison to the corresponding 3-alkyl-2,4-pentanediones with respect to the obtained yields of the corresponding substituted 3-cyano-2-pyridones.

Methyl orthocarboxylates as methylating agents of heterocycles

Methylation reactions occurring between trimethyl orthocarboxylates or N,N-dimethylcarboxamide dimethyl acetals and various hydroxylated heterocycles, involving a lactam-lactim tautomeric equilibrium, were investigated as an alternative to classic methyla

1-Alkylpyrid-2-one

Novel compounds belonging to the class of 3-carboxy (or the physiologically acceptable salts thereof), 3-carbalkoxy, and 3-carbamoyl-1-alkyl-4,6-disubstituted pyrid-2-ones. These compounds possess biological activity and in particular are gametocides and plant growth regulators. Novel 3-cyano-1-alkyl-4,6-disubstituted pyrid-2-ones are also disclosed as intermediates.