Sodium Carbonate → HCID 52913736, compound

HRID 594988Notes

Reaction equation

HRID 594988 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:10]2=[N:11][C:12]([NH:15][C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[N:13][CH:14]=[C:9]2[CH:8]=[N:7]1.[O:25]1[CH2:30][CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.CO>[O:25]1[CH2:26][CH:27]=[C:28]([C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[CH2:5][N:6]2[C:10]3=[N:11][C:12]([NH:15][C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)=[N:13][CH:14]=[C:9]3[CH:8]=[N:7]2)[CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 66765269HCID 66765269, compound

Product 1

HCID 52913736HCID 52913736, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

1-(3-iodobenzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (50 mg, 0.12 mmol), 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (29 mg, 1.2 eq), sodium carbonate (31 mg, 2.5 eq) and bis(diphenylphosphino)-ferrocenedichloropalladium(II)-DCM-complex (5 mg, 0.05 eq) in ACN/water (1:1, 2 mL) were heated in the microwave for 30 min at 130° C. The reaction mixture was diluted with methanol, passed through a thiol column, washed with methanol and evaporated. The residue was dissolved in DCM, the organic phase washed with water, dried over sodium sulfate and concentrated in vacuo to afford 1-(3-(3,6-dihydro-2H-pyran-4-yl)benzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine.

Workup

  1. washwashed with methanol
  2. customevaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washthe organic phase washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be5afb26d156431e837940b51590f388
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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