Sodium Hydroxide → HCID 18982861, compound

HRID 1440211Notes

Reaction equation

HRID 1440211 reaction equation
C([O:4][CH:5]([C:7]1[N:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[Cl:14])[CH3:6])(=O)C.[OH-].[Na+]>O1CCCC1>[Cl:13][C:9]1[C:8]([Cl:14])=[C:7]([CH:5]([OH:4])[CH3:6])[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22097406HCID 22097406, compound

Product 1

HCID 18982861HCID 18982861, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of tetrahydrofuran was dissolved 4.0 g of 6-(1-acetoxyethyl)-4,5-dichloropyrimidine, and 30 ml of a 1N-sodium hydroxide aqueous solution was slowly added dropwise to the solution under stirring. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour to complete the reaction. Then, the reaction mixture was extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting oily product was purified by silica gel column chromatography (Wako gel C-200 (trade name, manufactured by Wako Junyaku Co.), eluted by toluene:ethyl acetate=5:1) to obtain 2.8 g of the title compound as a pale yellow liquid.

Workup

  1. additionwas slowly added dropwise to the solution
  2. additionAfter the dropwise addition
  3. stirringthe mixture was further stirred at room temperature for 1 hour
  4. customthe reaction
  5. extractionThen, the reaction mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting oily product was purified by silica gel column chromatography (Wako gel C-200 (trade name, manufactured by Wako Junyaku Co.), eluted by toluene:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-1217bc3fa40244ee94c0a83690c27654
Source dataset
uspto-grants-1996_03
Patent number
US05498612

Reaction notes

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