2-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine → 3,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4326

Reaction equation

HRID 4326 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[N:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[N:3]=1>C(O)C.[Pd]>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:4]2[N:3]=[CH:2][N:7]([CH3:8])[C:6](=[N:9][C:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[CH3:18])[CH:5]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 1

HCID 201522932-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 201522633,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidineYield 26.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.5 g) in ethanol (20 ml) was added 10%-palladium on carbon (0.8 g). The mixture was stirred under hydrogen (1 atm) for 40 minutes. After removal of the catalist by filtration, the filtrate was evaporated in vacuo. The residue was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using chloroform. The fractions containing the desired compound were combined and evaporated in vacuo to give a residue, which was recrystallized from ethyl acetate to afford 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (0.36 g).

Workup

  1. customAfter removal of the catalist
  2. filtrationby filtration
  3. customthe filtrate was evaporated in vacuo
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo
  10. customto give a residue, which
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-be3baba0a63e43b69785207ba89bb350
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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