Isopropylamine → 4-(4-(isopropylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 44C (388 mg, 1.48 mmol) and propan-2-amine (0.14 mL, 1.63 mmol) in THF (10 mL) was added TEA (0.456 mL, 3.27 mmol). The resulting mixture was stirred at 30° C. overnight and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure, and dried. To the crude material was added iodotrimethylsilane (1.0 mL, 7.06 mmol) in tetramethylene sulfone (5 mL). The reaction mixture was heated at 80° C. overnight. The reaction was slowly poured into ice-water (5 mL). The precipitate was collected, washed with water, and purified by reverse phase HPLC (mobile phase: 0%-50% acetonitrile in 0.1% TFA aqueous solution during 40 minutes) to provide the title compound: 1H NMR (400 MHz, DMSO-D6) δ ppm 9.68 (1H, s, br), 8.55 (1H, s, br), 8.39 (1H, s), 8.35 (1H, s), 7.82 (2H, d), 6.88-6.94 (2H, m), 4.34-4.46 (1H, m), 1.28 (6H, d)

Provenance & Evidence