p-Toluenesulfonic acid → HCID 22504340, compound

HRID 1813922Notes

Reaction equation

HRID 1813922 reaction equation
C(O[C:4](=[O:26])[CH:5]([CH3:25])[CH2:6][C:7]1[C:8]([Cl:24])=[N:9][C:10]([CH3:23])=[N:11][C:12]=1[NH:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:24][C:8]1[C:7]2[CH2:6][CH:5]([CH3:25])[C:4](=[O:26])[N:13]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])[C:12]=2[N:11]=[C:10]([CH3:23])[N:9]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54037977HCID 54037977, compound

Product 1

HCID 22504340HCID 22504340, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-[4-chloro-2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-5-yl]-2-methyl-propionic acid ethyl ester (173 mg, 0.46 mmol) and p-TsOH (56 mg) in 10 ml of toluene was heated at reflux using Dean-stark trap apparatus for 9 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic extract was washed with brine, dried and concentrated to give 184 mg of the crude material. The crude material was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 95 mg of the title compound as white crystals, mp 136-139° C., after recrystallization from ethyl ether. 1H NMR (CDCl3) δ 6.95(s,1H), 6.94(s,1H), 3.25(dd,1H), 2.8-3.0(m,2H), 2.41(s,3H), 2.32(s,3H), 1.96(s,3H), 1.93(s,3H), 1.37(d,3H)ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 9 hours
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customto give 184 mg of the crude material
  11. customThe crude material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-50414c1d03484aaf819252b89c04da09
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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