Sodium hydride → 8-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

HRID 732080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732080
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][NH:17][C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30]Cl)[N:26]=2)[CH:22]=[CH:23][CH:24]=1>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30][N:17]3[CH2:16][CH2:15][CH2:14][N:13]4[C:9]([C:6]5[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=5)=[N:10][N:11]=[C:12]34)[N:26]=2)[CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

Produkt 1

HCID 670707678-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidineAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

32 mg (1.31 mmol) NaH was added to a solution of 193 mg (0.96 mmol) 3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine in 10 ml DMF at room temperature. After 10 min 200 mg (0.87mmol) 5-(3-chloro-phenyl)-3-chloromethyl-[1,2,4]oxadiazole was added to the reaction mixture. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with NH4Cl(sat) and extracted twice with EtOAc. The combined organic phases were washed with water, dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 111 mg (32%) of a white solid. 1H NMR (CDCl3), d (ppm): 2.24 (m, 2 H), 3.57 (m, 2 H) 4.15 (m, 2 H) 5.01 (s, 2 H) 7.46 (t, 1 H) 7.56 (d, 1 H) 7.62 (d, 2 H) 7.99 (d, 1 H) 8.10 (s, 1 H) 8.70 (d, 2 H).

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fdaa5fd19621477394410c05126284b4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

Notizen zur Reaktion

Wird geladen…