4,6-Dichloropyrimidine → 4-(6-Chloro-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester

HRID 448556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448556
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=1>C1COCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][C:25]2[CH:26]=[C:21]([Cl:20])[N:22]=[CH:23][N:24]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 709434,6-DichloropyrimidineHCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 467382884-(6-Chloro-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2a (0.76 g, 4.06 mmol) in 10 mL of THF at room temperature, was added potassium tert-butoxide (0.65 g, 1.4 eq). The resulting mixture was stirred at room temperature for 30 minutes then 4,6-dichloropyrimidine (0.8 g, 1.3 eq) was added. The reaction mixture was stirred at room temperature for 16 h then the solvent was removed under a stream of nitrogen. The residue was taken up with DCM and purified by flash chromatography (elution with 0-40% ethyl acetate and 0.1% TEA in hexanes) to give 0.51 g of 2b (42% yield).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customthe solvent was removed under a stream of nitrogen
  3. custompurified by flash chromatography (elution with 0-40% ethyl acetate and 0.1% TEA in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a8102f6e9c364aeaaa0e0a4230f2088b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481731B2

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