Pyrrolidine → HCID 86610556, compound

Participants

Reaction Steps

(2R*,4S*)-4-{[3,5-Bis(trifluoromethyl)benzyl]-(5-bromopyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (250 mg) is dissolved in toluene (2 ml), and thereto are added tris(dibenzylideneacetone)dipalladium (6.9 mg), sodium tert-butoxide (54.8 mg), 2-(di-tert-butylphosphino)biphenyl (9.0 mg) and pyrrolidine (47 μl). The mixture is stirred at room temperature for 45 minutes under nitrogen flow, then heated to 80° C, and stirred for 18 hours. After cooling to room temperature, ether is added to the reaction solution. The mixture is filtered, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=9:1→7:3) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(pyrrolidin-1-yl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (158.5 mg). MS (m/z): 653 [M+H]+.

Provenance & Evidence