Potassium Hydroxide → HCID 57753033, compound

HRID 225448Notes

Reaction equation

HRID 225448 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13]3[N:14]=[C:15]([CH3:27])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][C:25]#N)[CH2:20][CH2:19]4)[C:12]=3[S:11][C:10]=2[CH3:28])=[C:4]([CH3:29])[CH:3]=1.[OH-:30].[K+].[OH:32]S([O-])(=O)=O.[K+]>CCO.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13]3[N:14]=[C:15]([CH3:27])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:32])=[O:30])[CH2:20][CH2:19]4)[C:12]=3[S:11][C:10]=2[CH3:28])=[C:4]([CH3:29])[CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 11178857HCID 11178857, compound

Product 1

HCID 57753033HCID 57753033, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile (350 mg) and KOH (492 mg) in a mixture of EtOH (1.5 mL) and H2O (1.0 mL) in a sealed tube was heated at 105° C. for 3 hours. After concentration of the reaction mixture under reduced pressure, 5% KHSO4 aqueous solution was added and extracted with CHCl3. The organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: CHCl3/methanol=20:1) to obtain the title compound (164 mg).

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: CHCl3/methanol=20:1)

Sources & evidence

ORD record
ord-3b2763fd6cd142e1b172eb5fc93aa1a4
Source dataset
uspto-grants-2009_07
Patent number
US07557111B2

Reaction notes

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