Potassium Hydroxide → HCID 21254974, compound

HRID 636430Notes

Reaction equation

HRID 636430 reaction equation
[OH-].[K+].[C:3]1([S:9]([C:12]2[C:13]([O:29][CH2:30][C:31](OCC)=[O:32])=[N:14][N:15]3[C:20]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:19][C:18]([CH3:28])=[N:17][C:16]=23)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O.O1CCOCC1.C1COCC1>[C:3]1([S:9]([C:12]2[C:13]([O:29][CH2:30][CH2:31][OH:32])=[N:14][N:15]3[C:20]([N:21]4[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]4)=[CH:19][C:18]([CH3:28])=[N:17][C:16]=23)(=[O:10])=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21254996HCID 21254996, compound

Product 1

HCID 21254974HCID 21254974, compoundYield 32,382.801%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

A solution of 0.126 g of KOH in 5 ml of H2O was added to a solution of 0.61 mg of ethyl 2-[3-benzenesulphonyl-5-methyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidin-2-yloxy]-acetate in 20 ml of dioxan/THF 1:1 and stirred at RT for 2.5 hrs. The reaction solution was evaporated and the residue was partitioned between H2O and CH2Cl2. The aqueous phase was washed three times with 30 ml of CH2Cl2,and the combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2,CH2Cl2/MeOH 9:1) of the residue and crystallization from EtOH yielded 0.18 g (18%) of 2-[3-benzenesulphonyl-5-methyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidin-2-yloxy]-ethanol as colorless crystals. M.p. 177.5-178°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between H2O and CH2Cl2
  3. washThe aqueous phase was washed three times with 30 ml of CH2Cl2,and the combined organic phases
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customChromatography (SiO2,CH2Cl2/MeOH 9:1) of the residue and crystallization from EtOH

Sources & evidence

ORD record
ord-337b8ef84c7e429383c4df176fce2c13
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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