5428-89-7

Usage

Uses

Used in Pharmaceutical Research:
5-Chloropyrimidin-2-amine is used as a key intermediate in the synthesis of various biologically active compounds. Its ability to form JAK2 inhibitors makes it a valuable reagent for the development of treatments for myeloproliferative disorders, which are a group of blood cancers characterized by the overproduction of blood cells.
Additionally, 5-Chloropyrimidin-2-amine is used as a building block in the creation of SIRT2 inhibitors. These inhibitors are being investigated for their potential to treat Huntington's disease, a neurodegenerative disorder that affects muscle coordination and cognitive abilities.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 567, 1942 DOI: 10.1021/ja01255a030

InChI:InChI=1/C4H4ClN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 36437-19-1 2-chloromalonaldehyde 
• 593-85-1 diguanidine carbonate 
• 87-56-9 mucochloric acid 
• 506-93-4 guanidine nitrate 
• 35034-15-2 2‐aminopyrimidine‐1‐oxide 

Downstream Products

• 68303-37-7 N-(5-chloro-pyrimidin-2-yl)-acetamide 
• 5433-20-5 N-(5-chloro-pyrimidin-2-yl)-benzenesulfonamide 
• 22536-67-0 2,5-dichloropyrimidine 
• 132635-70-2 N-(5-Chloro-pyrimidin-2-yl)-2-methyl-benzamidine 
• 118644-47-6 N-(2,6-Dichlorbenzoyl)-N'-(5-chlorpyrimidin-2-yl)harnstoff 
• 111604-44-5 N-(2,6-Difluorbenzoyl)-N'-(5-chlorpyrimidin-2-yl)harnstoff 
• 105094-60-8 N-(5-Chlorpyrimidin-2-ylaminosulfonyl)benzamid 
• 126556-12-5 1-(2-Chloro-benzoyl)-3-(5-chloro-pyrimidin-2-yl)-thiourea 
• 126556-09-0 1-Benzoyl-3-(5-chloro-pyrimidin-2-yl)-thiourea 
• 126556-10-3 1-(5-Chloro-pyrimidin-2-yl)-3-(4-methyl-benzoyl)-thiourea 
• 120821-48-9 N-(5-Chloro-pyrimidin-2-yl)-4-methyl-benzamide 
• 126556-13-6 1-(4-Chloro-benzoyl)-3-(5-chloro-pyrimidin-2-yl)-thiourea 
• 120821-50-3 4-Chloro-N-(5-chloro-pyrimidin-2-yl)-benzamide 
• 126556-11-4 1-(5-Chloro-pyrimidin-2-yl)-3-(4-methoxy-benzoyl)-thiourea 

Relevant academic research and scientific papers

IF5 affects the final stage of the Cl-F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C-S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.

N-Chloro-N-methoxybenzenesulfonamide: A Chlorinating Reagent

A structurally simple and reactive chlorinating reagent, N-chloro-N-methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3-Diketones, β-keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes, and aromatic amines were successfully chlorinated, and the products were obtained in good to high yields.

CFBSA: a novel and practical chlorinating reagent

A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.

HETEROAROMATIC AMIDES AS INHIBITOR OF FACTOR XA

This application relates to heteroaromatic amides (or a pharmaceutically acceptable salt thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

DIAZOTIZATION OF SOME AMINODIAZINE N-OXIDES

Diazotization of a number of aminopyrazine and aminopyrimidine N-oxides affords intermediate diazonium compounds which can be converted to the corresponding bromo and chloro analogs in the presence of the appropriate halide ions.In some instances, electrophilic aromatic substitution takes place prior to the diazotization step.Nucleophilic halogenation accompanying deoxygenation occurs with 2-aminopyrimidine N-oxide in the same manner as described for some 3-amino-1,2,4-triazine 2-oxides.