Dimethylformamide → HCID 23115989, compound

HRID 1666554Notes

Reaction equation

HRID 1666554 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[N:31]=[CH:30][C:29]([C:32]([O:34]C3C=CC=CC=3)=O)=[CH:28][N:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[N:27]=[CH:28][C:29]([C:32]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:34])=[CH:30][N:31]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 23115993HCID 23115993, compound

Product 1

HCID 23115989HCID 23115989, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Piperidine (0.02 ml, 0.20 mmol) was added to a dimethylformamide solution (1.0 ml) of 2-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-(phenoxycarbonyl)pyrimidine (40 mg, 0.100 mmol), and stirred at room temperature for 12 hours. Water was added to the reaction mixture 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 partitioning thin-layer chromatography (hexane:ethyl acetate=3:7) to obtain the entitled compound (38 mg, 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. customthrough partitioning thin-layer chromatography (hexane:ethyl acetate=3:7)

Sources & evidence

ORD record
ord-c648977cfcfe41ff8d3fb274e71d9c7b
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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