Dimethylformamide → HCID 23130819, compound

HRID 1173785Notes

Reaction equation

HRID 1173785 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Cl[C:25]1[N:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=1>O>[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:25]3[N:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 786071,4'-BipiperidineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 23130819HCID 23130819, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(Piperidin-1-yl)piperidine (342 mg, 2.03 mmols) and cesium carbonate (764 mg, 2.34 mmols) were added to DMF solution (10 ml) of 2-chloro-5-bromopyrimidine (300 mg, 1.56 mmols), and stirred at room temperature for 16 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, chloroform/methanol=100/3) to obtain the entitled compound (349 mg, 69%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (C-300, chloroform/methanol=100/3)

Sources & evidence

ORD record
ord-04b24a24487a43b5a11b700525ce49f5
Source dataset
uspto-grants-2010_11
Patent number
US07834182B2

Reaction notes

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