Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile

HRID 514893

Reaktionsgleichung

Reaktionsgleichung von HRID 514893
[C-]#N.[Na+].C1N2CC[N:6](CC2)[CH2:5]1.[Br:12][C:13]1[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=1>CS(C)=O.O>[Br:12][C:13]1[CH:14]=[N:15][C:16]([C:5]#[N:6])=[N:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 6066655-Bromo-2-chloropyrimidine

Produkt 1

HCID 6865465-Bromopyrimidine-2-carbonitrileAusbeute 345,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of NaCN (0.849 g, 17.32 mmol) and DABCO (0.390 g, 3.48 mmol) in a mixture of DMSO (4 ml) and H2O (9 ml) was added a solution of 5-bromo-2-chloropyrimidine (3.05 g, 15.75 mmol) in DMSO (9 ml). The solution was stirred at room temperature overnight, and then diluted with water, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give 5-bromopyrimidine-2-carbonitrile (2.327 g, 12.01 mmol, 76% yield, 1H NMR (CDCl3 500 MHz): δ 8.94 (s, 2H)).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fd48237f294746c798ba3a3ce2577919
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108938B2

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