Pyrrolidine → HCID 10127419, Verbindung

To a solution of N-cyclopentyl-4-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine (24 mg, 0.057 mmol) in dichloromethane (3 mL) was added 3-chloroperoxybenzoic acid (15mg, 0.086 mmol) and the reaction mixture stirred for 1 hour. Pyrrolidine (3 mL) was added and the reaction mixture stirred for 2 hours before being diluted with dichloromethane. The organic phase was washed with saturated sodium bicarbonate, washed with brine, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 5% acetone in dichloromethane to yield N-cyclopentyl-4-[2-(4-fluorophenyl)-7-pyrrolidin-1-ylpyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine (15 mg, 59%). 1H NMR (CDCl3): δ 8.05 (d, 1H), 7.65 (d, 1H), 7.60 (dd, 2H), 7.43 (d,1H), 7.10 (t, 2H), 6.27 (d, 1H), 5.05 (d, 1H), 4.29 (m, 1H), 4.09 (t, 4H), 1.99 (m, 6H), 1.45–1.78 (m, 6H). MS m/z 444 (M+1).