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

Temperatur

30 °C

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)

1. washThe organic layer was washed with brine
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under reduced pressure
4. customdried
5. temperatureThe reaction mixture was heated at 80° C. overnight
6. customThe precipitate was collected
7. washwashed with water
8. custompurified by reverse phase HPLC (mobile phase: 0%-50% acetonitrile in 0.1% TFA aqueous solution during 40 minutes)

ORD-Eintrag

ord-4a4bbd6a832f4d239b05b65c0a22bc7c

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08232273B2