7637-33-4

Upstream product

• 4923-01-7 3-methyl-1H-1,2,4-triazol-5-amine 
• 123-54-6 acetylacetone 
• 83412-70-8 N-(4,6-dimethylpyrimid-2-yl)acetamide oxime 
• 767-15-7 2-Amino-4,6-dimethylpyrimidine 
• 83412-67-3 N,N-Dimethyl-N'-(4,6-dimethylpyrimid-2-yl)acetamidine 
• 54535-00-1 (5,7-dimethyl- [1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol 
• 1201687-89-9 2-(chloromethyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine 

Relevant academic research and scientific papers

Continuous flow enables metallaphotoredox catalysis in a medicinal chemistry setting: Accelerated optimization and library execution of a reductive coupling between benzylic chlorides and aryl bromides

Continuous flow has been used widely in process chemistry and academic settings for various applications. However, initial reaction discovery has generally remained "batch-exclusive" despite the existence of efficient, reproducible flow systems. We hereby disclose a workflow to bridge the gap between early medicinal chemistry efforts and process-scale development, showcased by the discovery and optimization of a metallaphotoredox-catalyzed cross-coupling between benzylic chlorides and aryl bromides, followed by two library syntheses of complex drug-like compounds.

Reactions of N-Heteroarylformamide Oximes and N-Heteroarylacetamide Oximes with N,N-Dimethylformamide Dimethyl Acetal. Synthesis of 2-Methyl-s-triazoloazines and N-Methylcyanoaminoazines

N-Heteroarylformamide oximes 3 (R = H) were converted with N,N-dimethylformamide dimethyl acetal (DMFDMA) into N-heteroaryl-N-methylcyanoamino compounds 5, as the main products.In some instances N-heteroarylcyanoamino compounds 4, cyanoimino compounds 7, and some other products, such as 9 and 10 were also formed.On the other hand, N-heteroarylacetamide oximes 3 (R = CH3) were cyclized under the same reaction conditions into 2-methyl-s-triazoloazines (6).N-Heteroarylacetamide O-methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R = CH3) and O-methylhydroxylamine.