Sodium Carbonate → 3-(2,3-dihydrobenzofuran-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 239636

반응식

HRID 239636 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.[O:12]1[C:16]2[CH:17]=[CH:18][C:19](B(O)O)=[CH:20][C:15]=2[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(O)C.O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[N:8][C:9]=4[NH2:11])[NH:4][N:3]=3)=[CH:20][C:15]=2[CH2:14][CH2:13]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 178508725HCID 178508725, 화합물

생성물 1

HCID 1785087033-(2,3-dihydrobenzofuran-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.70 g, 2.68 mmoles) in DMF (10 ml), ethanol (6 ml) and water (6 ml), 2,3-dihydrobenzofuran-5-boronic acid (0.527 g, 3.21 mmoles) and sodium carbonate (0.852 g, 8.04 mmoles) were added and the system is degassed for 30 min. Tetrakistriphenylphosphine Palladium (0.610 g, 0.528 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and 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 brown solid (0.198 g, 29% yield1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.42(s,1H), 8.18(s,1H), 7.48(s,1H), 7.36(d, J=8.1 Hz, 1H), 6.90(d, J=8.2 Hz, 1H), 4.61(d, J=8.7 Hz, 2H),3.27(d, J=8.7 Hz, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-055b622c187c4cc18ec3cdbaa6446188
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642607B2

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