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Sodium Carbonate → N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

HRID 929688
Notes
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Reaction equation

HRID 929688 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]2[N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:10]=[CH:11][C:3]=12.[C:18]([NH:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:21])[CH:19]=[CH2:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[N:5]=[C:4]2[N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:10]=[CH:11][C:3]2=[C:2]([C:25]2[CH:24]=[C:23]([NH:22][C:18](=[O:21])[CH:19]=[CH2:20])[CH:28]=[CH:27][CH:26]=2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 103213313-Acrylamidophenylboronic acidHCID 576542774,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 86677518N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamideYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (100 mg, 0.366 mmol), (3-acrylamidophenyl)boronic acid (70 mg, 0.366 mmol) and triphenylphosphine (4 mg, 0.015 mmol) were dissolved in a mixture of toluene (7 mL) and 1 M sodium carbonate (39 mg, 0.367 mmol). Palladium(II) acetate (2.0 mg, 0.009 mmol) was then added and the reaction mixture was stirred for 12 h at 80° C. The reaction mixture was then allowed to cool to room temperature and the solvent was removed in vacuo. The residue was dissolved in EtOAc (20 mL) and washed with water (10 mL). The organic layer was separated, the aqueous layer was extracted with EtOAc (20 ml), and organic layers were combined. The combined organic layers were washed with brine (20 mL), dried over Na2SO4 and then concentrated. The crude material was purified by flash chromatography (EtOAc/hexane 20%) to yield the title compound (70%). 1H NMR (400 MHz, CDCl3): δ 8.45 (m, 2H), 7.88 (d, 1H, J=8.0 Hz), 7.85 (d, 1H, J=8.0 Hz), 7.68 (s, 1H), 7.49 (t, 1H, J=8.0 Hz), 6.46 (m, 1H), 6.27 (m, 1H), 6.06 (d, 1H, J=10.4 Hz), 5.79 (d, 1H, J=10.0 Hz), 4.12 (m, 1H), 3.82 (t, 1H, J=10.0 Hz), 2.58 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.78 (m, 2H), 1.62 (m, 1H). ESI-MS: 384.10 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (20 ml), and organic layers
  7. washThe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography (EtOAc/hexane 20%)

Sources & evidence

ORD record
ord-0fe36bb15e334844867635cc1c4010d9
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296703B2

Reaction notes

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