[(R)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester → [(R)-1-(5-amino-2-chloro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester

Participants

Reaction Steps

A mixture of 3.3 g (0.011 mole) of [(R)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester (IV-102) in 150 mL of ethyl acetate and 0.8 g of 10% palladium on carbon catalyst was stirred under an atmosphere of hydrogen until hydrogen uptake was complete. The mixture was filtered through a pad of Celite, washing the filter pad with dichloromethane. The filtrate was concentrated under reduced pressure to give [(R)-1-(5-amino-2-chloro-pyrimidin-4-yl)-pyrrolidin-2-yl]-acetic acid methyl ester (V-102), which also contained a small amount of (R)-9-chloro-2,3,3a,4-tetrahydro-1H,6H-6,8,10,10b-tetraaza-benzo[e]azulen-5-one. This material was used directly in the next step without further purification.

Provenance & Evidence