Methyl iodide → 6-(3,4-dimethoxyphenyl)-2-methyl-4-[N-methyl-N-(2,4,6-trimethylphenyl)amino]pyrimidine

HRID 4336

Reaction equation

HRID 4336 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:28]C(C)([O-])C.[K+].CI>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([N:18]([CH3:28])[C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 201522766-(3,4-Dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 201522796-(3,4-dimethoxyphenyl)-2-methyl-4-[N-methyl-N-(2,4,6-trimethylphenyl)amino]pyrimidineYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenylamino)pyrimidine (1.0 g) in N,N-dimethylformamide (15 ml) were added potassium tert-butoxide (0.37 g) and methyl iodide (0.34 ml), and the mixture was stirred at ambient temperature for 1.5 hours. Then the mixture was poured into ice-water (200 ml) and stirred for an hour. The precipitates were collected, washed with water, dried in the air, and recrystallized from ethanol to give 6-(3,4-dimethoxyphenyl)-2-methyl-4-[N-methyl-N-(2,4,6-trimethylphenyl)amino]pyrimidine (0.58 g).

Workup

  1. stirringstirred for an hour
  2. customThe precipitates were collected
  3. washwashed with water
  4. customdried in the air
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7a100c5c6f4546fe8ba2e190fe4324e2
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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