Cornforth reagent → N-[4-(4-fluorophenyl)-5-[(E)-3-oxoprop-1-enyl]-6-propan-2-ylpyrimidin-2-yl]-N-methylmethanesulfonamide

Participants

Reaction Steps

Methyl (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl-amino)pyrimidin-5-yl]propen-1-ol (5.1 g) was added to molecular sieves (1 g) in dichloromethane (50 ml) and stirred for 15 min at room temperature. A solution of pyridinium dichromate (6.07 g) in dichloromethane (20 ml) was added to the above reaction mixture and continued stirring for 5 h at room temperature. After completion of the reaction, the reaction mass was filtered through a column of silica gel (230-400 mesh) and the eluate was distilled under reduced pressure to yield a semi-solid compound, which was crystallized from Hexane : Ethyl acetate (95 : 5 v/v) to yield (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-propenal.

Provenance & Evidence