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

HRID 1619440

Reaktionsgleichung

Reaktionsgleichung von HRID 1619440
CC(C)([O-])C.[K+].[CH:7]([C:10]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[O:12][N:11]=1)([CH3:9])[CH3:8].[Cl:22][C:23]1[C:28]([CH3:29])=[C:27](Cl)[N:26]=[CH:25][N:24]=1>C1COCC1>[Cl:22][C:23]1[N:24]=[CH:25][N:26]=[C:27]([O:21][CH:18]2[CH2:17][CH2:16][N:15]([C:13]3[O:12][N:11]=[C:10]([CH:7]([CH3:9])[CH3:8])[N:14]=3)[CH2:20][CH2:19]2)[C:28]=1[CH3:29]

Komponenten

5

Edukt 3

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OLHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazoleAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Potassium tert-butoxide (478 mg, 0.00426 moles) was added to a solution of 1-(3-iso-propyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol (0.9 gm, 0.00426 moles) and 4,6-dichloro-5-methylpyrimidine (690 mg, 0.00426 moles) in dry THF (30 ml) at 0° C. and the reaction mixture was stirred for 20 hours at 30° C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 900 mg product as off white solid.

Aufarbeitung

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2596b292049147a481c0de98949b0136
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772302B2

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