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

HRID 1476163노트

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HRID 1476163 반응식
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

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178508725HCID 178508725, 화합물

생성물 1

HCID 1784899393-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 27%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

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=7.8Hz, 1H), 7.23(d, J=7.5 Hz, 1H), 7.18(d, J=2.4Hz, 1H), 7.04 (dd, J=8.0,1.8 Hz, 1H), 3.81(s, 3H).

후처리

  1. additionwas added under nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

출처 및 근거

ORD 기록
ord-2cf4926719944927b89dabd9eb7933eb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018375B2

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