Water → HCID 178508616, compound

HRID 432236Notes

Reaction equation

HRID 432236 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[C@H:29]1[CH2:32][C@@H:31]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:30]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:35]([O:34][CH2:33][C@H:31]1[CH2:32][C@H:29]([N:16]2[C:17]3=[N:18][CH:19]=[N:20][C:21]([NH2:23])=[C:22]3[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)=[N:15]2)[CH2:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 178505328HCID 178505328, compoundHCID 178508717HCID 178508717, compound

Product 1

HCID 178508616HCID 178508616, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.452 g, 0.00149 mol) in N,N-dimethylformamide (10 mL) was reacted with cis 3-[(benzyloxy)methyl]cyclobutyl methanesulfonate (0.483 g, 0.00179 mol) and cesium carbonate (0.582 g, 0.00179 mol) at 70° C. for two 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 trans 1-{3-[(benzyloxy)methyl]cyclobutyl}-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.325 g, 0.000681 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-cd2aefa09b2e40a385a1b159c2768675
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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