52476-88-7

Upstream product

• 1780-26-3 2,4-dichloro-2-methylpyrimidine 
• 1194-22-5 2-methyl-4,6-dihydroxypyrimidine 

Downstream Products

• 415698-40-7 1-(4-methylphenyl)ethanone (6-chloro-2-methylpyrimidin-4-yl)hydrazone 
• 1480674-49-4 7-chloro-5-methyl-3-phenyl[1,2,4]triazolo[4,3-c]pyrimidine 
• 1466918-10-4 C₁₂H₈Cl₂N₄ 
• 1484459-62-2 C₁₃H₁₁ClN₄O 
• 1598383-97-1 7-chloro-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-c]pyrimidine 
• 1598383-98-2 7-chloro-2-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-c]pyrimidine 
• 1598384-00-9 7-chloro-2-(2-methoxyphenyl)-5-methyl-[1,2,4]triazolo[1,5-c]pyrimidine 
• 330992-40-0 benzaldehyde (6-chloro-2-methylpyrimidin-4-yl)hydrazone 
• 415698-42-9 2-chlorobenzaldehyde (6-chloro-2-methylpyrimidin-4-yl)hydrazone 
• 330992-27-3 4-methoxybenzaldehyde (6-chloro-2-methylpyrimidin-4-yl)hydrazone 

Relevant academic research and scientific papers

Synthesis of 8-Bromo-7-chloro[1,2,4]triazolo[4,3- C ]pyrimidines, Their Ring Rearrangement to [1,5- C ] Analogues, and Further Diversification

8-Bromo-7-chloro[1,2,4]triazolo[4,3-c]pyrimidines were prepared by bromine-mediated oxidative cyclization of the aldehyde-derived hydrazones. The structure of one such product was unambiguously confirmed by single-crystal X-ray analysis. While the C-5 unsubstituted 1,2,4-triazolo[4,3-c]pyrimidine chemotype is extremely susceptible to ring isomerization at ambient conditions, the C-5-substituted analogues were found to be quite stable, permitting isolation in pure form. Nevertheless, they can still be converted into the 1,2,4-triazolo[1,5-c]pyrimidines by base- or acid-promoted Dimroth rearrangement. The presence of halogen functionalities on the pyrimidine nucleus renders the products useful as versatile synthetic intermediates for the easy diversification, as evidenced by palladium-catalyzed Kumada cross-couplings and Buchwald-Hartwig amination, as well as direct aromatic substitution.

IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives

Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1,2,4]triazolo[4,3-c]pyrimidine derivatives 5a-o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6a-o in moderate to high yields.

ANTIPROLIFERATIVE PYRIMIDYL, FUSED PYRIMIDYL AND PYRIMIDYL HYDRAZONES

The present invention is related to a novel series of pyrimidyl or fused pyrimidyl hydrazones. Compounds of Formula (I) wherein A is selected from the group consisting of Formulas (A1), (A2), (A3), (A4), (A5) are useful for the treatment and/or prevention of a proliferative disease.

Triazolopyrimidine cannabinoid receptor 1 antagonists

The present application describes compounds according to both Formulas I and II, pharmaceutical compositions comprising at least one compound according to either Formula I or II and optionally one or more additional therapeutic agents, and methods of treatment using the compounds according to Formulas I and II both alone and in combination with one or more additional therapeutic agents. The compounds have the following general formulas: including all prodrugs, solvates, pharmaceutically acceptable salts and stereoisomers, wherein R1, R2, R3, R4 and R5 are described herein.