39977-44-1

Basic information

• Product Name: METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE
• Synonyms: METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE;METHYL-6-HYDROXYMETHYL-2-PYRIDINE-CARBOXYLATE;Methyl 6-(hydroxymethyl)picolinate;6-Hydroxymethyl-pyridine-2-carboxylic acid methyl ester;methyl 6-(hydroxymethyl)pyridine-2-carboxylate;Methyl-6-hydroxymethyl-2-carboxylate;Methyl 6-hydroxyMethyl-2-pyridine carboxylic acid;2-hydroxymethylpyridine-6-carboxylic acid methyl ester
• CAS NO: 39977-44-1
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 1312995-182-4
• Mol File: 39977-44-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 327.251 °C at 760 mmHg
• Flash Point: 151.716 °C
• Appearance: White/Solid
• Density: 1.244
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.03±0.10(Predicted)
• CAS DataBase Reference: METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE(39977-44-1)
• EPA Substance Registry System: METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE(39977-44-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 39977-44-1(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white solid

Uses

Methyl 6-(Hydroxymethyl)-2-pyridinecarboxylate is a chemical compound used in the synthesis of Losartan (L470500) derivatives as AT1 antagonists in the preparation of antihypertensive agents. Also used to prepare telomerase inhibitors for in vivo inhibitory activity.

Synthesis

Into a 100-mL round-bottom flask, was placed a solution of 2,6-dimethyl pyridine-2,6- dicarboxylate (950 mg, 4.87 mmol, 1.00 equiv) in a solvent mixture of methanol (33.2 mL) and dichloromethane (14.2 mL). NaB (185 mg, 5.02 mmol, 1.00 equiv) was added to the reaction mixture in several batches at 0°C. The resulting solution was stirred overnight at room temperature, and then it was quenched by the addition of 50 mL of NC1 (aq.). The resulting solution was extracted with 2x50 mL of dichloromethane and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1-2: 1) as eluent to yield 750 mg (92%) of methyl 6-(hydroxymethyl)pyridine-2-carboxylate as a white solid.

InChI:InChI=1/C8H9NO3/c1-12-8(11)7-4-2-3-6(5-10)9-7/h2-4,10H,5H2,1H3

Upstream product

• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 

Downstream Products

• 220040-48-2 methyl 6-(chloromethyl)pyridine-2-carboxylate 
• 933791-33-4 2-hydroxymethyl-6-(1-hydroxy-1-methylethyl)pyridine 
• 135450-43-0 1-(6-(hydroxymethyl)pyridin-2-yl)ethan-1-one 
• 1332367-80-2 6,6'-((ethane-1,2-diylbis(benzylazanediyl))bis(methylene))dipicolinic acid 
• 1332367-79-9 dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate 

Relevant articles and documents

Py-Macrodipa: A Janus Chelator Capable of Binding Medicinally Relevant Rare-Earth Radiometals of Disparate Sizes

Nuclear medicine leverages different types of radiometals for disease diagnosis and treatment, but these applications usually require them to be stably chelated. Given the often-disparate chemical properties of these radionuclides, it is challenging to find a single chelator that binds all of them effectively. Toward addressing this problem, we recently reported a macrocyclic chelator macrodipa with an unprecedented "dual-size-selectivity"pattern for lanthanide (Ln3+) ions, characterized by its high affinity for both the large and the small Ln3+ (J. Am. Chem. Soc, 2020, 142, 13500). Here, we describe a second-generation "macrodipa-type"ligand, py-macrodipa. Its coordination chemistry with Ln3+ was thoroughly investigated experimentally and computationally. These studies reveal that the Ln3+-py-macrodipa complexes exhibit enhanced thermodynamic and kinetic stabilities compared to Ln3+-macrodipa, while retaining the unusual dual-size selectivity. Nuclear medicine applications of py-macrodipa for chelating radiometals with disparate chemical properties were assessed using the therapeutic 135La3+ and diagnostic 44Sc3+ radiometals representing the two size extremes within the rare-earth series. Radiolabeling and stability studies demonstrate that the rapidly formed complexes of these radionuclides with py-macrodipa are highly stable in human serum. Thus, in contrast to gold standard chelators like DOTA and macropa, py-macrodipa can be harnessed for the simultaneous, efficient binding of radiometals with disparate ionic radii like La3+ and Sc3+, signifying a substantial achievement in nuclear medicine. This concept could enable the facile incorporation of a breadth of medicinally relevant radiometals into chemically identical radiopharmaceutical agents. The fundamental coordination chemistry learned from py-macrodipa provides valuable insight for future chelator development.