Dimethylformamide → HCID 11290761, compound

HRID 736043Notes

Reaction equation

HRID 736043 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:12]1([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]3[N:29]=[CH:28][C:27](Br)=[CH:26][N:25]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]1=[O:37]>[Cu](I)I.O>[CH:12]1([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]3[N:29]=[CH:28][C:27]([N:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]4=[O:37])=[CH:26][N:25]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 231159615-Bromo-2-[(1-cyclopentylpiperidin-4-yl)oxy]pyrimidine

Product 1

HCID 11290761HCID 11290761, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Potassium carbonate (40 mg) and copper iodide (40 mg) were added to a DMF solution (5 ml) of 2-(1-cyclopentylpiperidin-4-yloxy)-5-bromopyrimidine (130 mg) and 1H-pyridin-2-one (19 mg), and stirred at 150° C. for 3 hours. The reaction mixture was cooled to room temperature, water was added to it and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1) to obtain the entitled compound (11 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-dac3951e80554953810b41d2fdb5c6f4
Source dataset
uspto-grants-2009_09
Patent number
US07595316B2

Reaction notes

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