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

Reaktionsgleichung

Reaktionsgleichung von HRID 4326
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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 201522633,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidineAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-be3baba0a63e43b69785207ba89bb350
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725600

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