Ethanol → 5-Ethoxycarbonyl 4-ethoxy 2-ethyl pyrimidine

HRID 1413437Notes

Reaction equation

HRID 1413437 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([CH2:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[Na].[CH2:16]([OH:18])[CH3:17]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:18][CH2:16][CH3:17])=[N:8][C:9]([CH2:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 702Ethanol3×HCID 5360545SodiumHCID 12363083Ethyl 4-chloro-2-ethylpyrimidine-5-carboxylate

Product 1

HCID 129016925-Ethoxycarbonyl 4-ethoxy 2-ethyl pyrimidineYield 68%

Procedure

To a solution cooled to 0° C. of 64.5 g of 5-ethoxycarbonyl 4-chloro 2-ethyl pyrimidine obtained in the preceding stage, in 200 ml of ethanol, was slowly added a solution of 7.75 g of sodium in 200 ml of ethanol, this being stirred for 15 min. after the addition. Then the solution was acidified to a pH≃3 with hydrochloric ethanol≃6.5 N, and the solvent was evaporated. The residue was diluted in water, extracted with chloroform, dried on sodium sulfate and the solvent evaporated. The residue was distilled and 46.7 g of the expected product were obtained.

Workup

  1. additionafter the addition
  2. customthe solvent was evaporated
  3. additionThe residue was diluted in water
  4. extractionextracted with chloroform
  5. customdried on sodium sulfate
  6. customthe solvent evaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-34a9c3398b6d4d9db31cff6d0452648c
Source dataset
uspto-grants-1981_02
Patent number
US04250178

Reaction notes

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