Water → HCID 22346881, compound

HRID 432230Notes

Reaction equation

HRID 432230 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.CS(O[CH:29]1[CH2:32][C:31](=[CH:33][CH2:34][CH3:35])[CH2:30]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[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])[N:16]([CH:29]3[CH2:32][C:31](=[CH:33][CH2:34][CH3:35])[CH2:30]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 22346726HCID 22346726, compoundHCID 178508717HCID 178508717, compound

Product 1

HCID 22346881HCID 22346881, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.743 g, 0.00245 mol) in N,N-dimethylformamide (20 mL) was reacted with 3-propylidenecyclobutyl methanesulfonate (0.699 g, 0.00367 mol) and cesium carbonate (0.866 g, 0.00367 mol) at 70° C. for three days. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (2×20 mL) and brine (20 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica using dichloromethane/methanol (98:2). The solvent was removed in vacuo to give 3-(4-phenoxyphenyl)-1-(3-propylidenecyclobutyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.655 g, 0.00165 mol) as a tan solid.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organic layers were washed with water (2×20 mL) and brine (20 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d23bfc9f5e2047699a7a2c9db9f6d948
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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