Sodium Carbonate → HCID 69203296, compound

HRID 898044Notes

Reaction equation

HRID 898044 reaction equation
C(O)(=O)C.I[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH2:15])[N:8]([C@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][O:24][CH3:25])[CH2:17]2)[N:7]=1.[CH3:26][C:27]1[CH:28]=[C:29]([CH3:52])[C:30]2[O:34][C:33]([NH:35][C:36]3[CH:41]=[CH:40][C:39](B4OC(C)(C)C(C)(C)O4)=[CH:38][CH:37]=3)=[N:32][C:31]=2[CH:51]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:15][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[N:8]([C@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][O:24][CH3:25])[CH2:17]3)[N:7]=[C:6]([C:39]3[CH:38]=[CH:37][C:36]([NH:35][C:33]4[O:34][C:30]5[C:29]([CH3:52])=[CH:28][C:27]([CH3:26])=[CH:51][C:31]=5[N:32]=4)=[CH:41][CH:40]=3)[C:14]=12

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 11581347(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amineHCID 69203470HCID 69203470, compound

Product 1

HCID 69203296HCID 69203296, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-3-iodo-1-[1-(2-methoxyethyl)-3-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate (0.64 g, 0.0014 mol), N-(5,7-dimethyl-1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.64 g, 0.00175 mol, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.081 g, 0.00007 mol) and sodium carbonate (0.37 g, 0.0035 mol) in N,N-dimethylformamide (15 mL) and water (7 mL) was heated at 80° C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature, and the solvent was removed under the reduced pressure. The residue was partitioned between water (25 mL) and dichloromethane (50 mL). The aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure to leave a brownish oil, which was purified by flash column chromatography on silica using 2%-10% methanol/dichloromethane as a mobile phase to give (S)-N2-(4-{4-amino-1-[1-(2-methoxyethyl)-3-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine (0.60 g, 0.0012 mol).

Workup

  1. temperatureto cool to ambient temperature
  2. customthe solvent was removed under the reduced pressure
  3. customThe residue was partitioned between water (25 mL) and dichloromethane (50 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (3×50 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvents were evaporated under the reduced pressure
  8. customto leave a brownish oil, which
  9. customwas purified by flash column chromatography on silica using 2%-10% methanol/dichloromethane as a mobile phase

Sources & evidence

ORD record
ord-e9393e8ec0a54366863b6975a95ad93d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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