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

HRID 1760658Notes

Reaction equation

HRID 1760658 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) δ 1.30 (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-ba444f4bb7ba46489395901a4268ccb2
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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