159715-63-6

Upstream product

• 5333-86-8 ethyl benzimidate hydrochloride 
• 2450-71-7 Propargylamine 
• 100-47-0 benzonitrile 

Downstream Products

• 170564-77-9 5-ethyl-6-hydroxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone 
• 158713-69-0 5-ethyl-2-phenyl-3-(prop-2-ynyl)-6-(trifluoromethyl)-4(3H)-pyrimidinone 
• 827-43-0 4-methyl-2-phenyl-1H-imidazole 
• 21194-81-0 4-benzyl-2-phenyl-1H-imidazole 
• 192802-91-8 5-ethyl-2-phenyl-3-propargyl-6-trifluoromethanesulfonyloxy-4(3H)-pyrimidinone 

Relevant academic research and scientific papers

Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine

Preliminary results of an original approach to 4-substituted-2-phenylimidazoles starting from readily available N-propargyl-benzamidine and aryl halides are reported. Best yields were obtained using aryl halides bearing an electron-withdrawing group. Plausible mechanisms are also discussed.

Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles

Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.

Investigating Scale-Up and Further Applications of DABAL-Me3 Promoted Amide Synthesis

Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h-1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones.

Regiocontrolled synthesis of 3-substituted-6-trifluoromethyl-4(3H)-pyrimidinones

Direct reaction of a variety of N-monosubstituted benzamidines with 4,4,4-trifluoroacetoacetate esters substituted at the 2-position with methyl, ethyl or methoxy afforded moderate to good yields of herbicidal 3-substituted-6-trifluoromethyl-4(3H)-pyrimidinones. Lower yields were obtained with the corresponding 4,4-difluoroacetoacetate esters and the reaction failed with nonfluorinated β-ketoesters. In addition to benzamidines, 3- and 4-pyridylcarboxamidines reacted successfully. The reaction tolerated propyl, allyl, propargyl and phenyl substituents on the amidine nitrogen.