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

HRID 1518312Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[N:9]=[CH:10][C:3]=12.[CH3:19][CH:20]([NH2:22])[CH3:21].I[Si](C)(C)C>C1COCC1.CCOC(C)=O.C1S(=O)(=O)CCC1>[CH:20]([NH:22][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:9]=[CH:10][C:3]=12)([CH3:21])[CH3:19]

Participants

Conditions

Temperature: 30 °C

Procedure

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)

Workup

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

Sources & evidence

ORD record: ord-4a4bbd6a832f4d239b05b65c0a22bc7c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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