Water → HCID 22346824, compound

HRID 432367Notes

Reaction equation

HRID 432367 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]([C:38]([O:40][CH2:41][CH3:42])=[O:39])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:30]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH:29]3[CH2:30][C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:32]3)[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 4

HCID 962WaterHCID 10796Cesium carbonateHCID 22347150HCID 22347150, compoundHCID 178508717HCID 178508717, compound

Product 1

HCID 22346824HCID 22346824, compoundYield 28,571.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.129 g, 0.00042 mmol) in N,N-dimethylformamide (5 mL) was reacted with diethyl 3-[(methylsulfonyl)oxy]-1,1-cyclobutanedicarboxylate (0.150 g, 0.00051 mmol) and cesium carbonate (0.166 g, 0.00051 mmol) at 70° C. for five days. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 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 diethyl 3-[4-amino-3-(4-phenoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1,1-cyclobutanedicarboxylate (0.060 g, 0.00012 mol) as a tan solid.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with water (2×10 mL) and brine (10 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-fe35f37541fc458f9c3092376c38e3db
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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