126378-42-5

Basic information

• Product Name: 4-METHOXY-3-(TRIISOPROPYLSILYL)PYRIDINE
• Synonyms: 4-METHOXY-3-(TRIISOPROPYLSILYL)PYRIDINE
• CAS NO: 126378-42-5
• Molecular Formula: C₁₅H₂₇NOSi
• Molecular Weight: 265.46648
• Mol File: 126378-42-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 331.2 °C at 760 mmHg
• Flash Point: 154.1 °C
• Appearance: /
• Density: 0.91 g/cm³
• PKA: 6.74±0.18(Predicted)
• CAS DataBase Reference: 4-METHOXY-3-(TRIISOPROPYLSILYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-3-(TRIISOPROPYLSILYL)PYRIDINE(126378-42-5)
• EPA Substance Registry System: 4-METHOXY-3-(TRIISOPROPYLSILYL)PYRIDINE(126378-42-5)

Safety Data

• Hazardous Substances Data: 126378-42-5(Hazardous Substances Data)

Usage

General Description

4-Methoxy-3-(triisopropylsilyl)pyridine is a chemical compound with the molecular formula C15H27NOSi. It is a pyridine derivative used in organic synthesis as a strong base and as a catalyst for a variety of reactions. The triisopropylsilyl group attached to the pyridine nitrogen atom makes the compound highly nucleophilic and allows for selective deprotonation of acidic hydrogen atoms in various organic molecules. The methoxy group adds to the compound's reactivity and stability. 4-Methoxy-3-(triisopropylsilyl)pyridine is commonly utilized in the synthesis of pharmaceuticals, agrochemicals, and materials science applications due to its versatile reactivity and ability to facilitate challenging transformations in organic chemistry.

Upstream product

• 620-08-6 4-methoxypyridine 
• 13154-24-0 triisopropylsilyl chloride 

Downstream Products

• 126378-69-6 2(R)-(2-methylpropyl)-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone 
• 144375-66-6 4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 135365-65-0 1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-4-methoxy-3-triisopropylsilanyl-pyridinium; chloride 
• 126378-58-3 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone 
• 144375-66-6 4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 138207-06-4 2-(3-Hydroxy-propyl)-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 

Relevant articles and documents

DIHYDROPYRIDONE AMIDES AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

Asymmetric synthesis of 2-alkyl(aryl)-2,3-dihydro-4-pyridones by addition of Grignard reagents to chiral 1-acyl-4-methoxypyridinium salts

The asymmetric synthesis of 2-alkyl(aryl)-2,3-dihydro-4-pyridones 3 by addition of various Grignard reagents to chiral 1-acyl-4-methoxypyridinium salts was studied in detail. Chiral pyridinium salts formed from 4-methoxy-3-(triisopropylsilyl)pyridine (2f), and (-)-8-arylmenthyl chloroformates, or (-)-trans-2-(α-cumyl)cyclohexyl chloroformate, gave the best results, with diastereomeric selectivities ranging from 60 to 94%. When 4-methoxy-3-(trialkylstannyl)pyridines were used, destannylated 2-alkyl-2,3-dihydropyridones 3a resulted in good yield. The size of the C-3 substituent, the auxiliary, the solvent, the reaction temperature, and the structure of the Grignard reagent were varied to determine their effect on the yield and the degree of asymmetric induction. The chiral auxiliary and the C-3 triisopropylsilyl group can be removed from 3f, and the auxiliary recovered, on treatment with sodium methoxide in methanol followed by aqueous acid. The resulting 2,3-dihydropyridones 8 are useful chiral building blocks for the enantioselective synthesis of various alkaloids.