105202-39-9

Upstream product

• 7033-39-8 5-bromo-1,3-dimethyluracil 
• 108-88-3 toluene 
• 31217-00-2 5-chloro-1,3-dimethyluracil 
• 3013-92-1 1,3-dimethyl-5-fluorouracil 
• 874-14-6 1,3-dimethyluracil 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 
• 85199-75-3 1,3-dimethyl-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione 
• 106-38-7 para-bromotoluene 

Relevant academic research and scientific papers

Pd(II)-catalyzed regioselective direct arylation of uracil via oxidative Heck reaction using arylboronic acids

A palladium catalyzed regioselective synthesis of 6-aryl uracils via oxidative Heck reaction (C-H bond functionalization) of uracils and arylboronic acids is reported. The method is simple, atom-economical, and high yielding.

Pd(II)-catalyzed regioselective direct arylation of uracil via oxidative Heck reaction using arylboronic acids

A palladium catalyzed regioselective synthesis of 6-aryl uracils via oxidative Heck reaction (C-H bond functionalization) of uracils and arylboronic acids is reported. The method is simple, atom-economical, and high yielding.

C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF 3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5- (trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs 2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.

Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C-H bond activation

A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C-H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives.

Palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil with aryl bromides: An electrophilic metalation-deprotonation with electrophilic arylpalladium intermediate

An efficient method of palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil was developed with a various range of aryl bromides including electron-deficient aryl bromides. 5-Aryluracil derivatives were obtained in moderate to good yields regiosele

Regioselective direct C-H arylations of protected uracils. Synthesis of 5- and 6-aryluracil bases

A new regioselective synthesis of 5- and 6-aryluracil bases based on direct C-H arylations of diverse 1,3-protected uracils has been developed. Benzyl-protected uracils were selected as the most practical in terms of stability during the arylation and fac

Switching the regioselectivity of direct C-H arylation of 1,3-Dimethyluracil

An interesting dichotomy in the regioselectivity and mechanism of direct C-H arylation of 1,3-dimethyluracil was observed. Its Pd-catalyzed reactions with diverse aryl halides in the absence of Cui lead preferentially to 5-aryluracils, while reactions in

Effect of bromides on the anomalous photoarylation of 5-halo-1,3-dimethyluracils

Photolysis of 5-chloro- and 5-fluoro-1,3-dimethyluracil in toluene in the presence of a bromide (e.g., p-dibromobenzene, 1,2-dibromoethane, and benzyl bromide) and an acid (trifluoroacetic acid, HBr) afforded 1,3-dimethyl-5-tolyluracils and the 6-isomers as the isomeric mixture. 5-Arylation occurred most favorably at ortho, while meta-isomers were preferential products in 6-arylation. The 5-isomers are suggested to be derived from uracils excited in the singlet states, while the 6-isomers are presumed to result from the uracils excited in the triplet states.

PHOTOLYSIS OF 5-BROMO-1,3-DIMETHYLURACIL IN SUBSTITUTED BENZENES

Photolysis of 5-bromo-1,3-dimethyluracyl in toluene, xylene and anisole afforded the anormalously substituted 6-aryl-1,3-dimethyluracils beside the expected products 5-aryl-1,3-dimethyluracils, while the reaction with veratrole occured exclusively at the 5-position of the uracil ring.