Ammonium Hydroxide → 7-Bromo-4-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-thieno[3,2-d]pyrimidine

HRID 532474

Reaktionsgleichung

Reaktionsgleichung von HRID 532474
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.[CH:12]([C:15]1[N:19]=[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:17][N:16]=1)([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C.[OH-].[NH4+]>C(O)(C)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:23]3[CH2:22][CH2:21][CH:20]([C:18]4[O:17][N:16]=[C:15]([CH:12]([CH3:14])[CH3:13])[N:19]=4)[CH2:25][CH2:24]3)[C:5]=2[S:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidineHCID 242088454-(3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl)piperidine

Produkt 1

HCID 682993907-Bromo-4-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-thieno[3,2-d]pyrimidineAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-bromo-4-chlorothieno[3,2-d]pyrimidine (100 mg) was added to isopropyl alcohol (3 mL), and 4-(3-isopropyl-[1,2,4]-oxadiazol-5-yl)piperidine (100 mg) and diisopropylethylamine (200 μL) were further added thereto. The reaction mixture was stirred at 100° C. for 12 hours. Then, the reaction mixture was mixed with saturated ammonium hydroxide solution and extracted twice with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a foamy residue. The residue was crystallized in the presence of diethyl ether to obtain the title compound (100 mg) as a whitish solid.

Aufarbeitung

  1. additionwere further added
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a foamy residue
  7. customThe residue was crystallized in the presence of diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5eb4980247e24944baaa66c8fdd70aa6
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853213B2

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