2,4,6-Trimethylaniline → HCID 54549582, compound

HRID 1737665Notes

Reaction equation

HRID 1737665 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:7](Cl)=[N:8][C:9]([CH3:13])=[N:10][C:11]=1[Cl:12])[CH3:2].[CH3:16][C:17]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:18]=1[NH2:19]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([Cl:12])=[N:10][C:9]([CH3:13])=[N:8][C:7]=1[NH:19][C:18]1[C:20]([CH3:25])=[CH:21][C:22]([CH3:24])=[CH:23][C:17]=1[CH3:16])[CH3:2]

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 52987903HCID 52987903, compound

Product 1

HCID 54549582HCID 54549582, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (2-methyl-4,6-dichloro-pyrimidine-5-yl)-acetic acid ethyl ester (1.470 g, 5.9 mmol) and 2,4,6-trimethylaniline (2.56 ml, 17.7 mmol), in 15 ml of dimethylsulfoxide was heated at 120° C. overnight and 138° C. for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give a brown oil. The oil was purified through silica gel column chromatography to give 1.070 g (52%) of the title compound as a tan solid. 1H NMR (CDCl3) δ1.30 (t, 3H), 2.14 (s, 6H), 2.32 (s, 3H), 2.37 (s, 3H), 3.79 (s, 2H), 4.23 (q, 2H), 7.00 (s, 2H), 7.02 (s, 1H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-1e0506068f20477885e9e057c3875bcc
Source dataset
uspto-grants-1999_10
Patent number
US05962479

Reaction notes

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