Sodium Hydroxide → 4-Chloro-5-ethoxycarbonyl-6-ethylpyrimidine

HRID 440457Notes

Reaction equation

HRID 440457 reaction equation
[CH2:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5](O)[C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].P(Cl)(Cl)([Cl:17])=O.[OH-].[Na+]>O>[Cl:17][C:5]1[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:3]([CH2:1][CH3:2])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178470080HCID 178470080, compound

Product 1

HCID 183578244-Chloro-5-ethoxycarbonyl-6-ethylpyrimidineYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 6-ethyl-4-hydroxypyrimidine-5-carboxylate (7.30 g, 37.21 mmol) was stirred under ice-cooling. Phosphorus oxychloride (11.41 g, 74.41 mmol) was added dropwise to it. After the addition, the mixture was stirred at 90° C. for 3 hours. After cooling to room temperature, the mixture was poured into ice-cooled water and adjusted to pH 10 with an aqueous solution of sodium hydroxide. The resulting mixture was extracted with methylene chloride and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2) to give the desired ethyl 4-chloro-6-ethylpyrimidine-5-carboxylate (3.50 g, 44%).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was poured into ice-
  5. extractionThe resulting mixture was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2)

Sources & evidence

ORD record
ord-dd18d132faad4662aeef4caf236e4eb8
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

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