188416-30-0

Basic information

• Product Name: 6-(1-BROMO-ETHYL)-4-CHLORO-5-FLUOROPYRIMIDINE
• Synonyms: Pyrimidine, 4-(1-bromoethyl)-2,6-dichloro-5-fluoro-
• CAS NO: 188416-30-0
• Molecular Formula: C6H4BrCl2FN2
• Molecular Weight: 273.9178
• Mol File: 188416-30-0.mol

Chemical Properties

• Boiling Point: 292.258 °C at 760 mmHg
• Flash Point: 130.553 °C
• Appearance: /
• Density: 1.817 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 6-(1-BROMO-ETHYL)-4-CHLORO-5-FLUOROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(1-BROMO-ETHYL)-4-CHLORO-5-FLUOROPYRIMIDINE(188416-30-0)
• EPA Substance Registry System: 6-(1-BROMO-ETHYL)-4-CHLORO-5-FLUOROPYRIMIDINE(188416-30-0)

Safety Data

• Hazardous Substances Data: 188416-30-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H4BrCl2FN2/c1-2(7)4-3(10)5(8)12-6(9)11-4/h2H,1H3

Upstream product

• 137234-85-6 2,4-dichloro-6-ethyl-5-fluoropyrimidine 

Relevant articles and documents

Preparation of triazoles by organometallic addition to ketones and intermediates therefor

A process for the preparation of a compound of the formula: or an acid addition or base salt thereof, wherein R is phenyl optionally substituted by 1 to 3 substituents each independently selected from halo and trifluoromethyl; R1 is C1-C6 alkyl; and “Het” is pyrimidinyl optionally substituted by 1 to 3 substituents each independently selected from C1-C4 alkyl, C1-C4 alkoxy, halo, oxo, benzyl and benzyloxy, comprising reacting a compound of the formula: with a compound of the formula wherein X is chloro, bromo or iodo, the reaction taking place in the presence of zinc; at least one of iodine or a Lewis acid; and an aprotic organic solvent: optionally further reacting the resulting compound with an acid or base to form the corresponding acid addition or base salt thereof.

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.