Cesium carbonate → HCID 89189131, compound

HRID 2207529Notes

Reaction equation

HRID 2207529 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][CH2:26][N:27]1[C:31](=[O:32])[CH2:30][S:29][C:28]1=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH2:25][CH2:26][N:27]3[C:31](=[O:32])[CH2:30][S:29][C:28]3=[O:33])[N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:9][CH:10]=3)[C:22]=12

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 16392506HCID 16392506, compoundHCID 178508717HCID 178508717, compound

Product 1

HCID 89189131HCID 89189131, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (800 mg, 2.64 mmol, 1.00 equiv) in N,N-dimethylformamide (25 mL), 3-(2-bromoethyl)-1,3-thiazolidine-2,4-dione (890 mg, 3.97 mmol, 1.50 equiv) and cesium carbonate (1.72 g, 5.26 mmol, 2.00 equiv). The resulting solution was stirred for 10 h at 80° C. in an oil bath. The reaction mixture was cooled with a water bath, diluted with 150 mL of ethyl acetate and washed with brine and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (100/1) to give 500 mg (42%) of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-1,3-thiazolidine-2,4-dione as a light yellow solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe reaction mixture was cooled with a water bath
  4. washwashed with brine and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. washeluted with dichloromethane/methanol (100/1)

Sources & evidence

ORD record
ord-a53a97ad0c2b474098e29647b144c297
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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