Potassium Carbonate → E-5-(2-Bromovinyl)-2,4-dimethoxypyrimidine

HRID 440718

Reaktionsgleichung

Reaktionsgleichung von HRID 440718
C(/[CH:4]=[CH:5]/[C:6]1[C:7]([O:14][CH3:15])=[N:8][C:9]([O:12][CH3:13])=[N:10][CH:11]=1)(O)=O.C([O-])([O-])=O.[K+].[K+].[Br:22]N1C(=O)CCC1=O>CN(C=O)C>[Br:22]/[CH:4]=[CH:5]/[C:6]1[C:7]([O:14][CH3:15])=[N:8][C:9]([O:12][CH3:13])=[N:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 688432(E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine

Produkt 1

HCID 15928608E-5-(2-Bromovinyl)-2,4-dimethoxypyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of E-5-(2-carboxyvinyl)-2,4-dimethoxypyrimidine (0.300 g; 1.43 retool) in dry DMF (5 ml) was added K2CO3 (0.45 g: 5.25 mmol). After stirring at ambient temperature for 15 min. a solution of N-bromosuccinimide (0.258 g; 1.45 mmol) in dry DMF (4 ml) was added dropwise over 10 min. The suspension was immediately filtered, the solid washed with DMF and the filtrate evaporated in high vacuum. The solid residue was purified by column chromatography by preloading on SiO2 and eluting with EtOAc-hexane (7:3, v/v). Product fractions were pooled and evaporated to give fine white crystals, yield 0.561 g (45%). FAB mass spectrum: m/z245 and 247 (M+H)+. Analysis, found: C,39.9; H, 3.6; N, 11.5% C8H9BrN2O2 requires C, 40.20; H, 3.70; N. 11.43%.

Aufarbeitung

  1. additionwas added dropwise over 10 min
  2. filtrationThe suspension was immediately filtered
  3. washthe solid washed with DMF
  4. customthe filtrate evaporated in high vacuum
  5. customThe solid residue was purified by column chromatography
  6. washeluting with EtOAc-hexane (7:3
  7. customevaporated
  8. customto give fine white crystals, yield 0.561 g (45%)

Quellen und Nachweise

ORD-Eintrag
ord-40eb5c33b73049cfb0ea5c5ad8a8ee30
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521163

Verknüpfte Notizen

Wird geladen…