Hydrochloric Acid → 3-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1484297Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C=O)C.C(O)C.O.ClCCl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.522 g, 2.0 mmoles) in DMF (10 ml), ethanol (5 ml) and water (5 ml), 3-methoxyphenylboronic acid (0.395 g, 2.59 mmoles) and sodium carbonate (1.05 g, 10 mmoles) were added and the system is degassed for 30 min. Palladium tetrakis triphenylphosphine (0.455 g, 0.39 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture neutralised with 1.5N HCl, extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as off-white solid (0.130 g, 27% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.57 (s, 1H), 8.20 (s, 1H), 7.46 (t, J=7.8 Hz, 1H), 7.23 (d, J=7.5 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 7.04 (dd, J=8.0, 1.8 Hz, 1H), 3.81 (s, 3H).

Workup

customthe system is degassed for 30 min
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record: ord-563754cfa8be488a938877e01af2fa11
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421209B2

Reaction notes

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