109371-19-9

Basic information

• Product Name: 4-methoxy-2,3,5-trimethylpyridine
• Synonyms: 4-methoxy-2,3,5-trimethylpyridine;Omeprazole Related Compound 2 (4-Methoxy-2, 3, 5-Trimethylpyridine)
• CAS NO: 109371-19-9
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 109371-19-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 227.2±35.0 oC (760 Torr), Calc.*
• Flash Point: 82.6±16.2 oC, Calc.*
• Appearance: /
• Density: 0.972±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.83±0.28(Predicted)
• CAS DataBase Reference: 4-methoxy-2,3,5-trimethylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-2,3,5-trimethylpyridine(109371-19-9)
• EPA Substance Registry System: 4-methoxy-2,3,5-trimethylpyridine(109371-19-9)

Safety Data

• Hazardous Substances Data: 109371-19-9(Hazardous Substances Data)

Usage

Description

4-Methoxy-2,3,5-trimethylpyridine is an organic compound characterized by its pyridine ring structure with specific substituents. It is a derivative of pyridine, featuring a methoxy group at the 4th position and methyl groups at the 2nd, 3rd, and 5th positions. 4-methoxy-2,3,5-trimethylpyridine is known for its unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Synthesis:
4-Methoxy-2,3,5-trimethylpyridine is used as a reagent for the synthesis of Omeprazole, a proton pump inhibitor. It plays a crucial role in the production process of this medication, which is widely prescribed for the reduction of stomach acids and treatment of conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and other acid-related disorders.
The compound's specific structural features allow it to participate in various chemical reactions, making it a versatile building block in the development of new drugs and pharmaceuticals. Its applications extend beyond the synthesis of Omeprazole, as it can be utilized in the creation of other bioactive molecules with potential therapeutic benefits.

InChI:InChI=1/C9H13NO/c1-6-5-10-8(3)7(2)9(6)11-4/h5H,1-4H3

Upstream product

• 67-56-1 methanol 
• 109371-18-8 4-chloro-2,3,5-trimethylpyridine 
• 73590-58-6 omeprazole 
• 109371-16-6 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 
• 109371-17-7 2,4-dichloro-3,5,6-trimethylpyridine 
• 73590-58-6 omeprazole 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 

Downstream Products

• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 84006-10-0 (chloromethyl)-4-methoxy-3,5-dimethylpyridine 
• 119141-88-7 esomeprazole 
• 73590-58-6 omeprazole 

Relevant articles and documents

Site selective syntheses of [3H]omeprazole using hydrogen isotope exchange chemistry

Omeprazole (Prilosec) is a selective and irreversible proton pump inhibitor used to treat various medical conditions related to the production of excess stomach acids. It functions by suppressing secretion of those acids. Radiolabeled compounds are commonly employed in the drug discovery and development process to support efforts including library screening, target identification, receptor binding, assay development and validation and safety assessment. Herein, we describe synthetic approaches to the controlled and selective labeling of omeprazole with tritium via hydrogen isotope exchange chemistry. The chemistry may also be used to prepare tritium labeled esomeprazole (Nexium), the active pure (S)-enantiomer of omeprazole.

Preparation method of 4-methoxy-2,3,5-trimethylpyridine

The invention belongs to the field of chemical intermediate preparation and specifically relates to a preparation method of 4-methoxy-2,3,5-trimethylpyridine. The preparation method comprises the following steps: 4-methoxy-2,3,5-trimethylpyridine-N-oxide is firstly obtained, and then 4-methoxy-2,3,5-trimethylpyridine is obtained. The preparation method has the characteristics of high yield, cheapraw material, simple process and good product quality. Thus, the preparation method has a certain application value.

Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.

A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.