N,N-Dimethylaniline → Ethyl (4-Chloro-2,6-dimethylpyrimidin-5-yl)acetate

HRID 1440447Notes

Reaction equation

HRID 1440447 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[N:3]=1.P(Cl)(Cl)([Cl:18])=O.CN(C)C1C=CC=CC=1>>[Cl:18][C:6]1[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[N:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135459178ethyl (2,6-dimethyl-3H-pyrimidin-4-on-5yl)acetate

Product 1

HCID 15296915Ethyl (4-Chloro-2,6-dimethylpyrimidin-5-yl)acetateYield 98%

Procedure

A mixture of ethyl (2,6-dimethyl-3H-pyrimidin-4-on-5yl)acetate (1.13 g, 5.4 mmol), phosphorous oxychloride (10 mL, and N,N-dimethylaniline (1.3 mL, 10.3 mmol) was heated under reflux for 3.5 h. The reaction mixture was concentrated, poured onto ice, and the resulting mixture was extracted with ether. The combined extracts were washed with water, dried (MgSO4), and concentrated to give 1.2 g (98%) of product as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 h
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured onto ice
  5. extractionthe resulting mixture was extracted with ether
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-480b5cd6321a4adb860968ea2c6d4862
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

Loading…