675-21-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1527, 1995 DOI: 10.1016/0040-4039(95)00076-O

InChI:InChI=1/C4H3FN2/c5-4-1-6-3-7-2-4/h1-3H

Upstream product

• 128229-03-8 (Z)-(2,3,3-trifluoro-l-propenyl)trimethylammonium iodide 
• 6313-33-3 formamidine hydrochloride 
• 109-89-7 diethylamine 
• 210169-03-2 2,4,6-tribromo-5-fluoropyrimidine 
• 4595-59-9 5-bromopyrimidine 

Downstream Products

• 1609735-13-8 1-(5-fluoropyrimidin-4-yl)cyclohexanecarbonitrile 

Relevant academic research and scientific papers

Pd-catalyzed nucleophilic fluorination of aryl bromides

On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.

Polyhalogenated heterocyclic compounds. Part 42. Fluorinated nitrogen heterocycles with unusual substitution patterns

Reductive replacement of fluorine in 3,5-dichloro-2,4,6-trifluoropyridine 2a and pentafluoropyridine 2 using DIBAL and LAH leads to useful syntheses of fluoro and chlorofluoro pyridine derivatives. Replacement of fluorine by bromine using a mixture of HBr and AlBr3 is extremely efficient, giving excellent routes to 2,4,6-tribromo-3,5-difluoropyridine 3. Bromofluoro-pyrimidine and -quinoxaline derivatives have also been efficiently synthesised from perfluorinated precursors. Catalytic hydrogenation of bromofluoro heterocycles gives high yields of the corresponding fluorinated heterocycles. Reactions of nucleophiles with 3 gives surprising results. Soft nucleophiles, e.g. PhSNa displace bromine whereas hard nucleophiles, e.g. MeONa, displace fluorine. British Crown Copyright 1998, Defence Evaluation and Research Agency. Published by the Royal Society of Chemistry with the permission of the controller of Her Britannic Majesty's Stationery Office.

Reactions of β-Fluorovinamidinium Salt with Bifunctional Hetero Nucleophiles. A New Synthetic Route to Fluorinated Heterocycles

β-Fluorovinamidium salt (2), readily prepared from N-(2,3,3-trifluoro-1-propenyl) trimethyl-ammonium iodide (1) and diethylamine, reacted with bifunctional hetero nucleophiles such as amidine and guanidine hydrochlorides in the presence of a base to afford regiospecifically monofluoronated pyrimidines 4 in good yields.The one-pot procedure starting from 1 was applicable for synthesizing heterocyclic compounds 4 in almost comparable yields.