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

HRID 1707956

Reaktionsgleichung

Reaktionsgleichung von HRID 1707956
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]C1CC(=O)NC1=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 38309BromosuccinimideHCID 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 mmol) 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. filtrationThe suspension was immediately filtered
  2. washthe solid washed with DMF
  3. customthe filtrate evaporated in high vacuum
  4. customThe solid residue was purified by column chromatography
  5. washeluting with EtOAc-hexane (7:3
  6. customevaporated
  7. customto give fine white crystals, yield 0.561 g (45%)

Quellen und Nachweise

ORD-Eintrag
ord-6ac405c0d0a744b1a8e8d2057c72b148
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356882

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