64074-29-9

Basic information

• Product Name: 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER;METHYL 2-PHENYLPYRIMIDINE-5-CARBOXYLATE
• CAS NO: 64074-29-9
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Mol File: 64074-29-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 161.5 - 163.5 deg C
• Boiling Point: 280.9 °C at 760 mmHg
• Flash Point: 123.7 °C
• Appearance: pale-yellow
• Density: 1.196 g/cm³
• PKA: -0.68±0.22(Predicted)
• Water Solubility: at 25 deg C (mg/L): 1789
• CAS DataBase Reference: 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER(64074-29-9)
• EPA Substance Registry System: 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER(64074-29-9)

Safety Data

• Statements: 22/36/37/38:
• Safety Statements: 22/26/36/37/39:
• Hazardous Substances Data: 64074-29-9(Hazardous Substances Data)

Usage

General Description

2-Phenyl-pyrimidine-5-carboxylic acid methyl ester is a chemical compound with the molecular formula C13H10N2O2. It is a methyl ester derivative of 2-phenyl-pyrimidine-5-carboxylic acid, which is a key component in the synthesis of pharmaceuticals and agrochemicals. 2-PHENYL-PYRIMIDINE-5-CARBOXYLIC ACID METHYL ESTER is a white to off-white crystalline powder that is used in the production of various drugs and pesticides. It is also used as a building block in the synthesis of more complex organic compounds, making it an important intermediate chemical in the pharmaceutical and agrochemical industries.

Upstream product

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

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 articles and documents

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.

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.