Sodium Iodide → (E)-5-(2-Bromovinyl)uracil

HRID 440719Notes

Reaction equation

HRID 440719 reaction equation
[Br:1]/[CH:2]=[CH:3]/[C:4]1[C:5]([O:12]C)=[N:6][C:7]([O:10]C)=[N:8][CH:9]=1.[Na+].[I-]>CC(O)=O>[Br:1]/[CH:2]=[CH:3]/[C:4]1[C:5](=[O:12])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 15928608E-5-(2-Bromovinyl)-2,4-dimethoxypyrimidine

Product 1

HCID 688297(E)-5-(2-Bromovinyl)uracilYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of E-5-(2-bromovinyl)-2,4-dimethoxypyrimidine (2.45 g; 10 mmol) in AcOH (10 ml) was added NaI (3.3 g; 2.2 eq.; 22 mmol) and the solution heated under reflux for 3 h. The hot mixture was filtered and diluted with water (15 ml). After cooling, the precipitated product was filtered off, washed with acetone (50 ml) and ether (20 ml) and dried to give a pale yellow powder (1.40 g, 65%). Mp>320° C.; 60 MHz 1H-NMR, DMSO-6d, δ: 7.60 (s, 1H, H-6); 7.30 (d, 1H, J=13 Hz, vinyl H); 6.80 (d, 1H, J=13 Hz, vinyl H).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 3 h
  3. filtrationThe hot mixture was filtered
  4. additiondiluted with water (15 ml)
  5. temperatureAfter cooling
  6. filtrationthe precipitated product was filtered off
  7. washwashed with acetone (50 ml) and ether (20 ml)
  8. customdried

Sources & evidence

ORD record
ord-23e2ef8cc43745359193bb1a9a8454ac
Source dataset
uspto-grants-1996_05
Patent number
US05521163

Reaction notes

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