2,4,6-Trimethylaniline → 6-(3,4-Dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine

HRID 4335

Reaction equation

HRID 4335 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[N:5]=[C:4]([CH3:18])[N:3]=1.[CH3:19][C:20]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:21]=1[NH2:22]>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]([CH3:18])[N:3]=[C:2]([NH:22][C:21]3[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=3[CH3:19])[CH:7]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 201522714-Chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

Product 1

HCID 201522766-(3,4-Dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine

Conditions

Temperature
120 °C

Procedure

The mixture of 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g) and 2,4,6-trimethylaniline (5.3 ml) was stirred at 120° C. for an hour. After cooled, the mixture was triturated with ethyl acetate. The precipitates were collected, and dissolved in chloroform. The solution was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated to give 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine (2.39 g).

Workup

  1. temperatureAfter cooled
  2. customthe mixture was triturated with ethyl acetate
  3. customThe precipitates were collected
  4. dissolutiondissolved in chloroform
  5. washThe solution was washed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-c718f36c041c43afbe95ad940fc057c9
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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