69081-08-9

Basic information

• Product Name: ethyl 4,6-dimethyl-2-methylaminopyridine-3-carboxylate
• CAS NO: 69081-08-9
• Molecular Weight: 208.26
• Mol File: 69081-08-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: ethyl 4,6-dimethyl-2-methylaminopyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,6-dimethyl-2-methylaminopyridine-3-carboxylate(69081-08-9)
• EPA Substance Registry System: ethyl 4,6-dimethyl-2-methylaminopyridine-3-carboxylate(69081-08-9)

Safety Data

• Hazardous Substances Data: 69081-08-9(Hazardous Substances Data)

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 1068-57-1 acetic acid hydrazide 
• 937-39-3 2-phenylacetylhydrazine 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 
• 74-89-5 methylamine 
• 622849-35-8 2-ethoxycarbonylmethyl-2-hydroxy-1,4,6-trimethyl-1,2-dihydropyrimidine 
• 75-04-7 ethylamine 
• 100-46-9 benzylamine 
• 313050-27-0 C₈H₁₄N₄O 
• 26275-64-9 1H-pyrazole-3-carbohydrazide 
• 140-87-4 Cyanoacetohydrazide 
• 3184-13-2 L-ornithine hydrochloride 

Relevant articles and documents

Formation of 2-pyridone in the process of the enamine rearrangement of pyrimidinium salts

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Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts

We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and C-pyrazolyl-substituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine- 3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine.

Novel route for the transformation of a pyrimidine ring using hydrazides

It has been shown from X-ray structural analytical data that the reaction of 2-ethoxycarbonylmethyl-1,4,6-trimethylpyrimidinium iodide with carboxylic acid hydrazides gives pyrazolo[1,5-a]pyrimidine derivatives and not the isomeric triazolo[4,3-a]pyridines previously reported. This novel and previously unreported rearrangement of 1,2-dialkylpyrimidinium salts occurs via recyclization of the pyrimidine ring with inclusion of a fragment of the nucleophilic reagent into the transformation product. 2006 Springer Science+Business Media, Inc.

Synthesis of nicotinic acid derivatives by the reaction of salts of 1-alkyl-4,6-dimethyl-2-pyrimidinylacetic acid esters with amines

A study was carried out on the enamine rearrangement of iodoalkylates of the ethyl ester of 4,6-dimethyl-2-pyrimidinylacetic acid to give ethyl esters of 2-alkylamino-4,6-dimethylnicotinic acid, which proceeds upon the action of various amines. The reaction with amines containing an alkyl substituent different from that at the quaternized nitrogen atom of the pyrimidinium salt leads to the formation of products of rearrangement and transamination. In the presence of water, the rearrangement is accompanied by the formation of the ethyl ester of 1,2-dihydro-2-oxo-4,6-dimethylnicotinic acid.