122372-10-5

Upstream product

• 5750-76-5 2,4,5-trichloropyrimidine 
• 98-80-6 phenylboronic acid 
• 960-16-7 tributylphenylstannane 

Downstream Products

• 37428-97-0 2,4,5-triphenylpyrimidine 
• 25095-48-1 2,4-diphenylpyrimidine 
• 901311-75-9 5-chloro-2,4-diphenylpyrimidine 

Relevant academic research and scientific papers

Microwave-assisted, efficient and regioselective Pd-catalyzed C-phenylation of halopyrimidines

We herein report that flash heating microwave irradiation is a helpful tool in the formation of arylpyrimidines from the corresponding halopyrimidines. The palladium-catalyzed cross-coupling reactions of 2,4-di- and 2,4,5-trihalopyrimidines with phenylboronic acid under the above conditions are described. By use of the appropriate catalyst and the adequate halopyrimidine, good regioselectivity can be achieved in the 2-, 4-, or 5-positions of the heterocycle. In addition, we show that this methodology is ameneable for the stepwise preparation of mono-, di-, and triphenylpyrimidines.

Regiochemistry in Pd-Catalysed Organotin Reactions with Halopyrimidines

Chlorines in activated pyrimidine position is replaced by carbon substituents in Pd-catalysed reactions with organotin compounds.The 4(6)-position is more reactive than the 2-position allowing for regioselective coupling in 2,4(6)-dihalopyrimidines.A bromine substituent is required for coupling in the benzenoid 5-position.In 5-bromo-2,4-dichloropyrimidine the 4-chlorine is replaced before the 5-bromine and the latter before the 2-chloro substituent, all in a regioselective manner.The methodology can be used to introduce functionalized carbon substituents into any pyrimidine position.