Diisopropylethylamine → [1-(2-Methyl-pyrimidin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 451408Notes

Reaction equation

HRID 451408 reaction equation
[C:1]([N:8]1CCC(N)C[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[N:17]=1.C([N:26]([CH2:30][CH3:31])[CH:27]([CH3:29])C)(C)C>O1CCOCC1.O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]1[CH2:29][CH2:27][N:26]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[N:17]=2)[CH2:30][CH2:31]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67343389[1-(2-Methyl-pyrimidin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of Boc-4-aminopiperidine (715.3 mg, 3.5 mmol), 4-chloro-2-methylpyrimidine (521 mg, 3.85 mmol) and N,N-diisopropylethyl amine (899 L, 5.25 mmol) in dioxane (14 mL) was heated to 150° C. in the microwave for 30 minutes. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound was obtained after stirring of the crude product with diethyl ether and drying as white crystals (649.5 mg, 64%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d23cd134480144c9ab18247b9b85fa32
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…