N,N-Diethylaniline → HCID 19902835, compound

HRID 2372191Notes

Reaction equation

HRID 2372191 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-e899e480d2e542d2be374b2330c36bb8
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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