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

HRID 1476187Notes

Reaction equation

HRID 1476187 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.[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

Participants

7

Reactant 3

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

Product 1

HCID 1785087033-(2,3-dihydrobenzofuran-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 29%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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% yield 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.42(s,1H), 8.18(s,1H), 7.48(s,1H), 7.36(d, J=8.1Hz, 1H), 6.90(d, J=8.2Hz, 1H), 4.61(d, J=8.7Hz, 2H),3.27(d, J=8.7Hz, 2H).

Workup

  1. additionwas added under nitrogen atmosphere
  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

Sources & evidence

ORD record
ord-436b105ecd064d5aa37b6e94bdda279c
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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