Dimethylformamide → tert-Butyl 4-[(5-bromopyrimidin-2-yl)oxy]piperidine-1-carboxylate

HRID 1666539Notes

Reaction equation

HRID 1666539 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Cl[C:27]1[N:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=1>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:27]2[N:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23115964tert-Butyl 4-[(5-bromopyrimidin-2-yl)oxy]piperidine-1-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-t-butoxycarbonyl-4-hydroxypiperidine (408 mg, 2.03 mmol) and cesium carbonate (764 mg, 2.34 mmol) were added to a DMF solution (10 ml) of 2-chloro-5-bromopyrimidine (300 mg, 1.56 mmol), and stirred at room temperature for 14 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=10:1) to obtain the entitled compound (268 mg, 48%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  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, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a38f7e5444de4c97a75355d09989ea76
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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