134000-96-7

Usage

Uses

Used in Pharmaceutical Industry:
Pyrimidine, 2-chloro-5-fluoro-4-methyl(9CI) serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the creation of new drugs, potentially contributing to the development of treatments for a range of medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, Pyrimidine, 2-chloro-5-fluoro-4-methyl- (9CI) is utilized in the production of agrochemicals. Its role as an intermediate aids in the formulation of products designed to enhance crop protection and improve agricultural yields.
Used in Organic Synthesis:
Pyrimidine, 2-chloro-5-fluoro-4-methyl(9CI) is a versatile building block in organic synthesis, with potential applications across the chemical industry. Its ability to be modified and incorporated into more complex molecules makes it suitable for the development of a wide array of organic compounds.
Used in Dye and Pigment Production:
Pyrimidine, 2-chloro-5-fluoro-4-methyl(9CI) also finds use in the production of dyes and pigments, where its chemical properties contribute to the color and stability of these products. Its presence in these applications underscores its importance in the manufacturing of various consumer and industrial goods.

Upstream product

• 2927-71-1 2,4-dichloro-5-fluoropyrimidine 
• 954220-98-5 2,4-dichloro-5-fluoro-6-methyl-pyrimidine 
• 676-58-4 methylmagnesium chloride 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 1595144-31-2 (R)-N-(4-cyanophenylethyl)-1-(5-fluoro-4-methylpyrimidin-2-yl)piperidine-3-carboxamide 
• 1293283-27-8 2-(5-fluoro-4-methylpyrimidin-2-yl )-5-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole 

Relevant academic research and scientific papers

Synthesis method of 2-chloro-5-fluoro-6-methylpyrimidine

The invention relates to a synthesis method of 2-chloro-5-fluoro-6-methylpyrimidine, which comprises the following steps: dissolving sodium methoxide in methanol, adding urea, stirring, dropwisely adding ethyl 2-fluoroacetoacetate, and carrying out a reflux reaction for 2-3 hours to obtain an intermediate A; mixing the intermediate A, phosphorus oxychloride and organic alkali according to a weightratio of 1: (5-10): (0.3-2) for reaction, cooling the mixture, removing redundant phosphorus oxychloride, adding water for quenching extraction, drying, and concentrating to obtain a product B; and adding ethanol, zinc powder and acetic acid into the product B, carrying out a heating reflux reaction for 10-16 hours, cooling, filtering, evaporating to remove the ethanol, extracting with an organicsolvent, evaporating to dryness to obtain a crude product, and carrying out vacuum distillation to obtain a pure product C, namely the 2-chloro-5-fluoro-6-methylpyrimidine. The method has the effectsthat the yield is increased, the time is shortened, the operation is simple, and the post-treatment process is simplified.

Overcoming Time-Dependent Inhibition (TDI) of Cytochrome P450 3A4 (CYP3A4) Resulting from Bioactivation of a Fluoropyrimidine Moiety

Herein we describe structure-activity relationship (SAR) and metabolite identification (Met-ID) studies that provided insight into the origin of time-dependent inhibition (TDI) of cytochrome P450 3A4 (CYP3A4) by compound 1. Collectively, these efforts revealed that bioactivation of the fluoropyrimidine moiety of 1 led to reactive metabolite formation via oxidative defluorination and was responsible for the observed TDI. We discovered that substitution at both the 4- and 6-positions of the 5-fluoropyrimidine of 1 was necessary to ameliorate this TDI as exemplified by compound 19.

IMIDAZOPYRIDAZINE COMPOUNDS USEFUL AS MODULATORS OF IL-12, IL-23 AND/OR IFN ALPHA RESPONSES

Compounds having the following formula (I), or a stereoisomer or pharmaceutically-acceptable salt thereof, where R1, R2, R3, R4, and R5 are as defined herein, are useful in the modulation of IL-12, IL-23 and/or IFNα, by acting on Tyk-2 to cause signal transduction inhibition.

Discovery of trifluoromethyl(pyrimidin-2-yl)azetidine-2-carboxamides as potent, orally bioavailable TGR5 (GPBAR1) agonists: Structure-activity relationships, lead optimization, and chronic in vivo efficacy

Activation of the G-protein coupled receptor (GPCR) Takeda G-protein receptor 5 (TGR5), also known as G-protein bile acid receptor 1 (GPBAR1), has been shown to play a key role in pathways associated with diabetes, metabolic syndrome, and autoimmune disease. Nipecotamide 5 was identified as an attractive starting point after a high-throughput screen (HTS) for receptor agonists. A comprehensive hit-to-lead effort culminated in the discovery of 45h as a potent, selective, and bioavailable TGR5 agonist to test in preclinical metabolic disease models. In genetically obese mice (ob/ob), 45h was as effective as a dipeptidyl peptidase-4 (DPP-4) inhibitor at reducing peak glucose levels in an acute oral glucose tolerance test (OGTT), but this effect was lost upon chronic dosing.

TRPV3 Modulators

Disclosed herein are modulators of TRPV3 of formula (I) wherein X1, X2, R1, R2, Rx, and n are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also presented.

DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS

Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS

Certain disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane are described, which are useful as orexin inhibitors. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS

Disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

DISUBSTITUTED OCTAHY - DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS

Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

SUBSTITUTED CYCLOPROPYL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

Substituted cyclopropyl compounds of formula (I) are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. Pharmaceutically acceptable salts and solvates are included as well. The compounds are useful as agonists of the g-protein coupled receptor GPR-119.