Hexane → Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 271558

Reaktionsgleichung

Reaktionsgleichung von HRID 271558
[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.CCC[CH2:22][CH2:23][CH3:24].[CH3:25]COC(C)=O>CCO.C(N(CC)CC)C>[C:23]([O:8][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=2)[CH2:3][CH2:2]1)=[O:9])([CH3:22])([CH3:24])[CH3:25]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 131766Piperazine-1-carboxylic acidHCID 35727632-Chloro-5-ethylpyrimidine

Produkt 1

HCID 53305712Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To piperazine-1-carboxylic acid .tert.-butyl ester (3.543 mmol) in EtOH (13 ml), triethylamine (1.5 ml) and 2-chloro-5-ethyl-pyrimidine (3.540 mmol) are added. The mixture is refluxed with stirring for 6 h. After cooling at room temperature, the reaction mixture is quenched with an ice water and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and concentrated to give the product in 41% yield. Rf=0.45 (n-hexane:AcOEt=10:1) 1H NMR(400 MHz, CDCl3) δ 1.19 (t, 3H), 1.49 (s, 9H), 2.47 (q, 2H), 3.49 (dd, 4H), 3.76 (dd, 4H), 8.18 (s, 2H)

Aufarbeitung

  1. temperatureThe mixture is refluxed
  2. customthe reaction mixture is quenched with an ice water
  3. extractionextracted with AcOEt
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give the product in 41% yield

Quellen und Nachweise

ORD-Eintrag
ord-89bb9428f6594941ac30e5acc50f4b5d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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