Phosphorus oxychloride → Ethyl 3-(4-Chloro-2,6-dimethylpyrimidin-5-yl)propionate

HRID 1440451Notes

Reaction equation

HRID 1440451 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH3:16])[N:3]=1.P(Cl)(Cl)([Cl:19])=O>CN(C)C1C=CC=CC=1>[Cl:19][C:6]1[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH3:16])[N:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1359679873-(4-Hydroxy-2,6-dimethyl-pyrimidin-5-yl)-propionic acid ethyl ester

Product 1

HCID 14916837Ethyl 3-(4-Chloro-2,6-dimethylpyrimidin-5-yl)propionateYield 72%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineCatalyst

Procedure

A mixture of ethyl 3-(2,6-dimethyl-3H-pyrimidin-4-on-5yl)propionate (3.87 g, 0.017 mol), phosphorus oxychloride (40 mL), and N,N-dimethylaniline (10 drops) was heated under reflux for 2 h. The mixture was concentrated, cooled, and ice water was added. Solid KOH was added to bring the pH to 6 and the mixture was extracted with ether. The extracts were dried (MgSO4) and concentrated to give 2.95 g (72%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. temperaturecooled
  5. additionice water was added
  6. additionSolid KOH was added
  7. extractionthe mixture was extracted with ether
  8. dry with materialThe extracts were dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fb0415ddffe3422eb16e8c9c48896a82
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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