4,6-Dichloro-5-methylpyrimidine → 5-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1036800

Reaktionsgleichung

Reaktionsgleichung von HRID 1036800
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:16][C:17]1[C:22]([CH3:23])=[C:21](Cl)[N:20]=[CH:19][N:18]=1>C1COCC1.CC(C)([O-])C.[K+]>[Cl:16][C:17]1[C:22]([CH3:23])=[C:21]([O:15][CH:12]2[CH2:11][CH2:10][N:9]([C:7]3[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=3)[CH2:14][CH2:13]2)[N:20]=[CH:19][N:18]=1

Komponenten

5

Edukt 2

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Produkt 1

HCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazoleAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 23665647Potassium tert-butoxideLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-ol (3.65 g, 17 mmol) and 4,6-dichloro-5-methylpyrimidine (2.83 g, 17 mmol) in THF (70 mL), 1M potassium-t-butoxide in THF (16 mL, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 10 min. The crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v) to provide 4-chloro-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine as a solid (4.15 g, 71%). Exact mass calculated for C15H20ClN5O2337.13, found 338.2 (MH+).

Aufarbeitung

  1. customThe crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-1f34800992164151a3f8684e44b0c7bf
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546429B2

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