Potassium Hydroxide → N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (320 mg, 0.58 mmol) in methanol (5 mL) was added an aqueous solution of KOH (2 N, 5 mL). The mixture was heated at 100° C. for 3 h. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc. The extract was washed with H2O, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 30 mg (26%) of N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solid. 1H NMR (500 MHz, CD3OD): δ 11.93 (s, 1H), 11.41 (s, 1H), 9.40 (m, 1H), 7.80 (d, 2H), 7.69 (s, 1H), 6.60 (m, 2H), 6.27 (d, 2H), 5.63 (m, 1H), 1.88 (s, 1H), 1.45 (d, 3H), 0.94 (m, 2H), 0.71 (m, 2H); MS (ESI): m/z=395.1 [M+1]+.

Provenance & Evidence