Sodium Methoxide → HCID 12151205, compound

HRID 2415027Notes

Reaction equation

HRID 2415027 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4]([CH3:13])[N:3]=1.[CH3:14][O-:15].[Na+]>CO>[I:8][C:7]1[C:2]([O:15][CH3:14])=[N:3][C:4]([CH3:13])=[N:5][C:6]=1[C:9]([F:12])([F:11])[F:10]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12151204HCID 12151204, compound

Product 1

HCID 12151205HCID 12151205, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-5-iodo-2-methyl-6-trifluoromethylpyrimidine (23.0 g) was dissolved in methanol (150 ml) and sodium methoxide (30% methanol solution, 12.8 g) was added under ice cooling with stirring. After stirring over night at room temperature, the solvent was removed under reduced pressure. The residue was mixed with water and extracted with benzene, and then benzene layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate). The crude fraction was concentrated, and then washed with cold hexane to give 5-iodo-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (13.0 g) as colorless crystalline solid, mp 44-45° C.

Workup

  1. stirringAfter stirring over night at room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was mixed with water
  4. extractionextracted with benzene
  5. washbenzene layer was washed with water and brine
  6. dry with materialrespectively and dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  9. concentrationThe crude fraction was concentrated
  10. washwashed with cold hexane

Sources & evidence

ORD record
ord-e596de06b7b64463a2c3f604999587f1
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

Loading…