Tetrabutylammonium Fluoride → HCID 69182947, compound

HRID 2373230Notes

Reaction equation

HRID 2373230 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:25]=[C:24]2[N:26]([CH2:29][CH3:30])[N:27]=[CH:28][C:23]2=[C:22]([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH3:37])[CH:36]=2)[C:21]=1[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH2:29]([N:26]1[C:24]2=[N:25][C:20]([CH2:19][OH:18])=[C:21]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:22]([C:31]3[CH:32]=[N:33][CH:34]=[C:35]([CH3:37])[CH:36]=3)=[C:23]2[CH:28]=[N:27]1)[CH3:30]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69183134HCID 69183134, compound

Product 1

HCID 69182947HCID 69182947, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethyl 3-[6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (313 mg) in THF (10 ml) was added 1N tetrabutyl ammonium fluoride in THF (0.52 ml) at 0° C. and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (3:1) then a mixture of MeOH and CHCl3 (1:50) to give ethyl 3-[1-ethyl-6-(hydroxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (100 mg) as a yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (3:1)
  6. additiona mixture of MeOH and CHCl3 (1:50)

Sources & evidence

ORD record
ord-5471f4d39d4a4596ad4a3be3480c2776
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

Loading…