N,N-Diethylaniline → HCID 19902835, compound

HRID 2372225Notes

Reaction equation

HRID 2372225 reaction equation
[C:1]([C:4]1[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][C:7](O)=[N:8][CH:9]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:18])=O.CCN(C1C=CC=CC=1)CC>>[C:1]([C:4]1[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][C:7]([Cl:18])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178470323HCID 178470323, compound

Product 1

HCID 19902835HCID 19902835, compound

Procedure

A mixture of ethyl 5-acetyl-2-hydroxy-4-pyrimidinecarboxylate (2.91 g, 13.8 mmol), phosphoryl chloride (11 ml, 118.0 mmol) and diethylaniline (3 ml, 18.0 mmol) is heated to reflux under N2 for 45 min, after which it is cooled to RT and worked up. The residue is distilled, then dissolved in a small amount of methylene chloride and set aside to crystallize. The solid is then filtered, rinsed with methylene chloride and dried to give ethyl 5-acetyl-2-chloro-4-pyrimidinecarboxylate.

Workup

  1. temperatureis heated
  2. temperatureto reflux under N2 for 45 min
  3. distillationThe residue is distilled
  4. dissolutiondissolved in a small amount of methylene chloride
  5. customto crystallize
  6. filtrationThe solid is then filtered
  7. washrinsed with methylene chloride
  8. customdried

Sources & evidence

ORD record
ord-cc2b18ff08e14f2285a1b8d7cbf96df3
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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