64074-29-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyl-pyrimidine-5-carboxylic acid methyl ester is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be incorporated into the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Phenyl-pyrimidine-5-carboxylic acid methyl ester is used as a building block for the synthesis of pesticides. Its incorporation into the development of new agrochemicals can lead to the creation of more effective and targeted pest control solutions.
Used in Organic Synthesis:
2-Phenyl-pyrimidine-5-carboxylic acid methyl ester is used as a versatile intermediate in the synthesis of more complex organic compounds. Its reactivity and functional groups make it a valuable component in the development of advanced organic molecules for various applications in research and industry.

Upstream product

• 150017-46-2 methyl 1-amino-1H-pyrazole-4-carboxylate 
• 825-60-5 benzimidic acid ethyl ester 
• 618-39-3 benzamidin 
• 875554-08-8 methyl 1-trityl-1H-pyrazole-4-carboxylate 
• 51105-90-9 methyl pyrazole-4-carboxylate 
• 1670-14-0 benzamidine monohydrochloride 

Downstream Products

• 122773-97-1 2-phenylpyrimidine-5-carboxylic acid 
• 1217902-04-9 2-phenyl-5-(3-phenyl-1H-pyrazol-5-yl)pyrimidine 
• 1068968-64-8 2-phenyl-pyrimidine-5-carboxylic acid [1,2,4]triazol-4-ylamide 
• 1068969-31-2 [N'-(2-phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetamide 
• 1068969-30-1 [N'-(2-phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetic acid ethyl ester 
• 1068968-67-1 2-phenyl-pyrimidine-5-carboxylic acid piperidin-1-ylamide 
• 1068972-13-3 2-phenyl-pyrimidine-5-carboxylic acid (indol-1-yl)-amide 
• 1068969-33-4 2-phenyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide 
• 1068968-89-7 2-phenyl-pyrimidine-5-carboxylic acid N'-(2-oxo-piperidin-1-yl)-amide 
• 1068969-71-0 2-phenyl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide 
• 1068968-97-7 2-phenyl-pyrimidine-5-carboxylic acid (2,6-dimethyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-amide 
• 1068968-81-9 2-phenyl-pyrimidine-5-carboxylic acid N'-methyl-N'-[5-trifluoromethyl-pyridin-2-yl]-hydrazide 
• 1068968-50-2 2-phenyl-pyrimidine-5-carboxylic acid [6-(4-fluoro-phenyl)-3-oxo-2,5-dihydro-3H-1.2.4-triazin-4-yl]-amide 
• 1068969-03-8 3-{2,4-dioxo-3-[(2-phenyl-pyrimidine-5-carbonyl)-amino]-1,2,3,4-tetrahydro-pyrimidin-5-yl}-propionic acid methyl ester 

Relevant academic research and scientific papers

Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution

A comprehensive study of the reaction scope of methyl 1,2,3-triazine-5-carboxylate (3a) with alkyl and aryl amidines is disclosed, reacting at room temperature at remarkable rates (5 min, 0.1 M in CH3CN) nearly 10000-fold faster than that of unsubstituted 1,2,3-triazine and providing the product pyrimidines in high yields. C4 Methyl substitution of the 1,2,3-triazine (3b) had little effect on the rate of the reaction, whereas C4/C6 dimethyl substitution (3c) slowed the room-temperature reaction (24 h, 0.25 M) but displayed an unaltered scope, providing the product pyrimidines in similarly high yields. Measured second-order rate constants of the reaction of 3a-c, the corresponding nitriles 3e and 3f, and 1,2,3-triazine itself (3d) with benzamidine and substituted derivatives quantitated the remarkable reactivity of 3a and 3e, verified the inverse electron demand nature of the reaction (Hammett ρ = -1.50 for substituted amidines, ρ = +7.9 for 5-substituted 1,2,3-triazine), and provided a quantitative measure of the impact of 4-methyl and 4,6-dimethyl substitution on the reactivity of the methyl 1,2,3-triazine-5-carboxylate and 5-cyano-1,2,3-triazine core heterocycles.

Inverse electron demand diels-alder reactions of 1,2,3-triazines: Pronounced substituent effects on reactivity and cycloaddition scope

A systematic study of the inverse electron demand Diels-Alder reactions of 1,2,3-triazines is disclosed, including an examination of the impact of a C5 substituent. Such substituents were found to exhibit a remarkable impact on the cycloaddition reactivity of the 1,2,3-triazine without altering, and perhaps even enhancing, the intrinsic cycloaddition regioselectivity. The study revealed not only that the reactivity may be predictably modulated by a C5 substituent (R = CO2Me > Ph > H) but also that the impact is of a magnitude to convert 1,2,3-triazine (1) and its modest cycloaddition scope into a heterocyclic azadiene system with a reaction scope that portends extensive synthetic utility, expanding the range of participating dienophiles. Significantly, the studies define a now powerful additional heterocyclic azadiene, complementary to the isomeric 1,2,4-triazines and 1,3,5-triazines, capable of dependable participation in inverse electron demand Diels-Alder reactions, extending the number of complementary heterocyclic ring systems accessible with implementation of the methodology.

A general procedure for the synthesis of 2-substituted pyrimidine-5-carboxylic esters

A method for the synthesis of 2-substituted pyrimidine-5-carboxylic esters is described. The sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (3) has been found to react with a variety of amidinium salts to afford the corresponding 2-substituted pyrimidine-5-carboxylic esters.