Water → HCID 117770705, compound

HRID 1526310Notes

Reaction equation

HRID 1526310 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:41])[N:8]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH:9]=[C:10]([C:11]3[CH:16]=[C:15]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH2:19][CH2:18]4)[N:14]=[C:13]([CH3:33])[N:12]=3)[C:5]=2[NH:4][N:3]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[NH2:1][C:2]1[C:6]2[C:7](=[O:41])[N:8]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH:9]=[C:10]([C:11]3[CH:16]=[C:15]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)[N:14]=[C:13]([CH3:33])[N:12]=3)[C:5]=2[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 131733161HCID 131733161, compound

Product 1

HCID 117770705HCID 117770705, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-7-(6-(4-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)-5-(2-methylphenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step C (195 mg) in tetrahydrofuran (2.0 mL) was added tetrabutylammonium fluoride tetrahydrofuran solution (1 M, 0.679 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin layer silica gel chromatography (methanol/dichloromethane), and then HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)). To the obtained fraction was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (50.0 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by thin layer silica gel chromatography (methanol/dichloromethane)
  6. additionTo the obtained fraction was added saturated aqueous sodium hydrogen carbonate solution
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-246deacc590d47039c8a274bcf0496c9
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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