p-Toluenesulfonic acid → HCID 86688208, compound

HRID 1630339Notes

Reaction equation

HRID 1630339 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([O:22][CH3:23])[CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=2)=[C:17]([O:22][CH3:23])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 4592574-Bromo-2-methoxyanilineHCID 210775872-Chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine

Product 1

HCID 86688208HCID 86688208, compoundYield 914%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.5 g, 2.36 mmol), 4-bromo-2-methoxyaniline (0.72 g, 0.38 mmol) and p-toluene sulphonic acid (0.49 g, 2.6 mmol) in dioxane (10 mL) was heated at 100° C. for 2 h. The mixture was cooled, filtered and the solid washed with dioxane. The solid was dried in a vacuum oven to give crude N2-(4-bromo-2-methoxyphenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (1.31 g) which was used in the next step without any further purification.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe solid washed with dioxane
  4. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-d855ede85cc74c33a210bd91cf62f8e8
Source dataset
uspto-grants-2014_07
Patent number
US08791130B2

Reaction notes

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