N,N-Diethylaniline → Ethyl 3-(4-Chloro-2-methyl-6-trifluoromethylpyrimidin-5-yl)propionate

HRID 1440457Notes

Reaction equation

HRID 1440457 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]([C:16]([F:19])([F:18])[F:17])[N:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:33]>>[Cl:33][C:6]1[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([C:16]([F:19])([F:18])[F:17])[N:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 135449112HCID 135449112, compound

Product 1

HCID 10379842Ethyl 3-(4-Chloro-2-methyl-6-trifluoromethylpyrimidin-5-yl)propionate

Procedure

A mixture of ethyl 3-(2-methyl-6-trifluoromethyl-3H-pyrimidine-4-on-5-yl)propionate (0.61 g, 2.20 mmol), N,N-diethylaniline (0.33 g, 2.2 mmol), and POCl3 (8 mL) was heated under reflux for 2 h. The mixture was concentrated, poured onto ice, and extracted with ether. The combined extracts were dried (MgSO4) and concentrated to give 0.65 g of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. additionpoured onto ice
  5. extractionextracted with ether
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39b8801e585347aeb5aa13f94e954cef
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

Loading…