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

HRID 1707956

Reaction equation

HRID 1707956 reaction equation
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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38309BromosuccinimideHCID 688432(E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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%.

Workup

  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%)

Sources & evidence

ORD record
ord-6ac405c0d0a744b1a8e8d2057c72b148
Source dataset
uspto-grants-1994_10
Patent number
US05356882

Linked notes

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