137234-87-8

Basic information

• Product Name: 4-Ethyl-5-fluoro-6-hydroxypyrimidine
• Synonyms: 6-Ethyl-5-fluoropyrimidin-4(3H)-one;6-ETHYL-5-FLUORO-PYRIMIDIN-4-OL;4-ETHYL-5-FLUORO-6-HYDROXYPYRIMIDINE;6-Ethyl-5-fluoro-4(1H)-pyrimidinone;6-Ethyl-5-fluoropyrimidin-4-one;4(1H)-Pyrimidinone, 6-ethyl-5-fluoro- (9CI);4-hydroxy-5-fluoro-6-ethylpyrimidine;4-Ethyl-5 fluoro-6-hydroxypirimidine
• CAS NO: 137234-87-8
• Molecular Formula: C₆H₇FN₂O
• Molecular Weight: 142.1309832
• EINECS: 422-460-5
• Product Categories: PYRIMIDINE;APIs & Intermediate;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorine series
• Mol File: 137234-87-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 180.724 ºC at 760 mmHg
• Flash Point: 63.1 ºC
• Appearance: white or off white solid
• Density: 1.302 g/cm³
• Vapor Pressure: 0.883mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.52±0.50(Predicted)
• Water Solubility: 94.9g/L at 20℃
• CAS DataBase Reference: 4-Ethyl-5-fluoro-6-hydroxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethyl-5-fluoro-6-hydroxypyrimidine(137234-87-8)
• EPA Substance Registry System: 4-Ethyl-5-fluoro-6-hydroxypyrimidine(137234-87-8)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-50/53
• Safety Statements: 60-61
• HazardClass: IRRITANT
• Hazardous Substances Data: 137234-87-8(Hazardous Substances Data)

Usage

Description

4-Ethyl-5-fluoro-6-hydroxypyrimidine is a pyrimidine derivative characterized by its white powder form. It is a chemical compound with the potential to be utilized in the synthesis of various bio-active molecules, particularly those with antifungal properties.

Uses

Used in Pharmaceutical Industry:
4-Ethyl-5-fluoro-6-hydroxypyrimidine is used as a key intermediate compound for the preparation of broad-spectrum triazole antifungal agents. Its chemical structure allows for the development of drugs that can effectively target and combat a wide range of fungal infections, making it a valuable asset in the fight against various fungal diseases.
Used in Chemical Research:
As a pyrimidine derivative, 4-Ethyl-5-fluoro-6-hydroxypyrimidine also holds potential in chemical research, particularly in the fields of medicinal chemistry and drug discovery. Its unique structure can be further modified and explored to create new compounds with potential applications in various therapeutic areas, contributing to the advancement of pharmaceutical science.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H7FN2O/c1-2-4-5(7)6(10)9-3-8-4/h3H,2H2,1H3,(H,8,9,10)

Upstream product

• 759-67-1 2-fluoro-3-oxopentanoic acid ethyl ester 
• 3473-63-0 formamidine acetic acid 
• 2927-71-1 2,4-dichloro-5-fluoropyrimidine 
• 609-08-5 Diethyl methylmalonate 
• 100-39-0 benzyl bromide 
• 188416-27-5 2-chloro-6-ethyl-5-fluoro4-hydroxypyrimidine, ammonium salt 
• 77287-34-4 formamide 
• 137234-85-6 2,4-dichloro-6-ethyl-5-fluoropyrimidine 
• 130129-58-7 5-chloro-6-ethyl-4-hydroxypyrimidine 
• 24045-73-6 ethyl 2-chloro-3-oxopentanoate 

Downstream Products

• 137234-74-3 4-chloro-6-ethyl-5-fluoropyrimidine 
• 137234-63-0 (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 137234-62-9 voriconazole 
• 182230-43-9 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 188416-34-4 (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate 
• 188416-35-5 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 137234-63-0 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol 
• 188416-28-6 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane 

Relevant articles and documents

Preparation method of 6-ethyl-5-fluoro-4-chloropyrimidine

The invention provides a preparation method of 6-ethyl-5-fluoro-4-chloropyrimidine. The preparation method comprises the following steps of: preparation of 6-ethyl-5-chloro-4-hydroxypyrimidine; preparation of 6-ethyl-5-fluoro-4-hydroxypyrimidine; and finally, acquisition of 6-ethyl-5-fluoro-4-chloropyrimidine. According to the invention, cheap alpha-chloropropionyl ethyl acetate or alpha-chloropropionyl methyl acetate is used as the raw material, after ring closing, potassium fluoride is used for fluorination, and finally thionyl chloride is used for chlorination so as to obtain the high yield6-ethyl-5-fluoro-4-chloropyrimidine, and the reaction steps are simple and easy to control, the method is suitable for industrial production, such that a more valuable synthesis route is provided forpreparation of aprepitant, good social benefits and economic benefits can be brought about, and the economic value potential is great.

An improvement in synthesis of 6-ethyl-5-fluoro-pyrimidin-4-ol

An effective and simple method for the preparation of 6-ethyl-5- fluoropyrimidin-4-ol is reported. It used formamide instead of formamidine acetate. It is new cyclization for synthesis of 6-ethyl-5-fluoropyrimidin-4-ol.

Process development of voriconazole: A novel broad-spectrum triazole antifungal agent

In the synthesis of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1- yl)-2-butanol (voriconazole), the relative stereochemistry is set in the addition of a 4-(1-metalloethyl)-5-fluoropyrimidine derivative to 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone. The diastereo-control of this reaction has been examined by variation of pyrimidine substitution pattern and by changes in the metalation and reaction conditions. Excellent diastereoselection (12: 1) is obtained using an organozinc derivative of 6-(1-bromoethyl)-4-chloro-5-fluoropyrimidine. After removal of the chlorine from the pyrimidine ring, the absolute stereochemistry of voriconazole is established via a diastereomeric salt resolution process using (1R)-10-camphorsulfonic acid. Synthetic routes to the pyrimidine partner have also been evaluated. The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of methyl 3-oxopentanoate and cyclisation with formamidine acetate.