Phosphorus oxychloride → Ethyl 4-chloro-2-ethylpyrimidine-5-carboxylate

HRID 1413436Notes

Reaction equation

HRID 1413436 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][C:9]([C:11]1[C:12](O)=[N:13][C:14]([CH2:17][CH3:18])=[N:15][CH:16]=1)=[O:10])[CH3:7]>C(N(CC)CC)C>[CH2:6]([O:8][C:9]([C:11]1[C:12]([Cl:3])=[N:13][C:14]([CH2:17][CH3:18])=[N:15][CH:16]=1)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469771HCID 178469771, compound

Product 1

HCID 12363083Ethyl 4-chloro-2-ethylpyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

7.5 ml of triethylamine were slowly introduced into 300 ml of phosphorous oxychloride cooled to 0° C., then were added 30 g of 5-ethoxycarbonyl 4-hydroxy 2-ethyl pyrimidine (VII) prepared in the preceding stage and the suspension was brought up to 40° C. under nitrogen scavenging. After dissolution, the phosphorous oxychloride was evaporated and the residue diluted in a mixture of water and chloroform. This was decanted, the chloroform phase was twice washed with water, dried on sodium sulfate and the solvent evaporated. The raw product obtained, after checking the purity by thin layer chromatography, was reacted in the following stage 3.

Workup

  1. customprepared in the preceding stage
  2. customwas brought up to 40° C. under nitrogen scavenging
  3. dissolutionAfter dissolution
  4. customthe phosphorous oxychloride was evaporated
  5. additionthe residue diluted in a mixture of water and chloroform
  6. customThis was decanted
  7. washthe chloroform phase was twice washed with water
  8. customdried on sodium sulfate
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-ffd9be3dd206450d9b6d8d96b70394b1
Source dataset
uspto-grants-1981_02
Patent number
US04250178

Reaction notes

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