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

HRID 440718

Reaction equation

HRID 440718 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]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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 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 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%.

Workup

  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%)

Sources & evidence

ORD record
ord-40eb5c33b73049cfb0ea5c5ad8a8ee30
Source dataset
uspto-grants-1996_05
Patent number
US05521163

Linked notes

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