Sodium → 2-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine

HRID 705033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705033
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[N+:2]=[N-:3].[C:10]([C:12]1[N:17]=[C:16]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[CH:14][CH:13]=1)#[CH:11].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>O.C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N:1]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]4[N:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:15]=[CH:14][CH:13]=3)[N:3]=[N:2]2)[CH:5]=1

Komponenten

8

Edukt 4

HCID 5360545SodiumHCID 120666873-AzidopyridineHCID 54670067L-Ascorbic AcidHCID 866981402-(6-Ethynylpyridin-2-yl)pyrimidine

Produkt 1

HCID 675143582-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidineAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

100 mg (833 μmol) of 3-azidopyridine (for preparation see U.S. Pat. No. 4,775,762, CAUTION explosive!) and 151 mg (833 μmol) of 2-(6-ethynylpyridin-2-yl)pyrimidine were initially charged in a mixture of 1 ml of water and 1 ml of tert-butanol, 16.5 mg (83.3 μmol) of the sodium salt of L-ascorbic acid and 20.8 mg (83.3 μmol) of copper(II) sulfate pentahydrate were added, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was then added to water and extracted repeatedly with dichloromethane. The separated organic phases were then dried over magnesium sulfate, filtered and concentrated. Chromatographic purification gave 26.0 mg (10% of theory) of 2-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine.

Aufarbeitung

  1. additionwere added
  2. extractionextracted repeatedly with dichloromethane
  3. dry with materialThe separated organic phases were then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification

Quellen und Nachweise

ORD-Eintrag
ord-705fe5ee5bb84c67af6bb44fce99981c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173396B2

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