Diisopropylethylamine → HCID 67343276, compound

HRID 451412

Reaction equation

HRID 451412 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]=[C:20]([CH3:22])[N:19]=[CH:18][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]=[C:20]([CH3:22])[N:19]=[CH:18][N:17]=2)[CH2:30][CH2:31]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5817964-Chloro-6-methylpyrimidineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67343276HCID 67343276, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of Boc-4-aminopiperidine (613 mg, 3 mmol), 4-chloro-6-methylpyrimidine (433 mg, 3.3 mmol) and N,N-diisopropylethyl amine (771 L, 4.5 mmol) in dioxane (12 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 crude product was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 as eluent. The title compound was obtained as a light yellow solid (693 mg, 79%).

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
  6. customThe crude product was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 as eluent

Sources & evidence

ORD record
ord-6de883d95cf14582bc0237df04c0840d
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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