Acetic Anhydride → 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl acetate

Participants

Reaction Conditions

Reaction Steps

A solution of 40 g of 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrmidine-1-oxide [prepared as described in step (a) above] in 1 liter of acetic anhydride was added dropwise, whilst heating at 50° C., to 1.5 liters of acetic anhydride. After the addition was complete, the solution was stirred at 110° C. for 2 hours. At the end of this time, the mixture was cooled to room temperature, and the solvent was evaporated off under reduced pressure. 400 ml of a mixture of toluene and hexane were added to the resulting residue, the mixture was stirred, and the solvent was separated by decantation; these operations were repeated a further 2 times. The decanted solvents were combined and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography, using chloroform as the eluent, to give 39.3 g of the title compound as a colorless oil.

Provenance & Evidence