Water → HCID 86688070, compound

HRID 407866Notes

Reaction equation

HRID 407866 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:25]1[N:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][N:26]=1.O>CN(C=O)C>[CH2:31]([C:28]1[CH:27]=[N:26][C:25]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)=[N:30][CH:29]=1)[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 86688070HCID 86688070, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl piperidin-4-ylcarbamate (5.0 g, 25 mmol) and DIEA (13.0 mL, 74.9 mmol) in DMF (50 mL) was added 2-chloro-5-ethylpyrimidine (4.3 g, 30 mmol). This mixture stirred at 100° C. for 18 hours in a sealed tube. The mixture was poured into water (500 mL) and extracted into EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified over silica gel (100% EtOAc) to yield tert-butyl 1-(5-ethylpyrimidin-2-yl)piperidin-4-ylcarbamate (3.2 g, 10 mmol, 42%).

Workup

  1. extractionextracted into EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified over silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-70d5f79b3efc4cdca0352d9a7c49f2c2
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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