Triethylamine → Ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylate

HRID 4679

Reaktionsgleichung

Reaktionsgleichung von HRID 4679
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8](=[CH:14]N(C)C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.Cl.[C:24]([NH2:27])(=[NH:26])[CH3:25].C(N(CC)CC)C>C(O)C>[CH3:25][C:24]1[N:27]=[C:6]([C:5]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67170Acetamidine monohydrochlorideHCID 53710889Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate

Produkt 1

HCID 20151431Ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31 g), acetoamidine hydrochloride (13.3 g) and triethylamine (16.2 g) in ethanol (200 ml) was refluxed for 10 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The separatedorganic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl ether to give ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylate (14 g).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. washThe separatedorganic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-341f97577ef543daa52fec737b242a18
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727073

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