2-Amino-4,6-dimethoxypyrimidine → Methyl 3 [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]-2-thiophenecarboxylate

HRID 256265

Reaktionsgleichung

Reaktionsgleichung von HRID 256265
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH3:12][O:13][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])=[O:15]>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:25]([NH:24][S:21]([C:20]2[CH:19]=[CH:18][S:17][C:16]=2[C:14]([O:13][CH3:12])=[O:15])(=[O:22])=[O:23])=[O:26])[N:7]=1

Komponenten

4

Edukt 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 1572962-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl ester

Produkt 1

HCID 13390186Methyl 3 [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]-2-thiophenecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 1.5 g of 2-amino-4,6-dimethoxypyrimidine in 30 ml of anhydrous acetonitrile was added 2.7 g of 2-methoxycarbonyl-3-thiophenesulfonyl isocyanate with stirring at ambient temperature. All of the solid reactant dissolved and after twenty minutes of stirring a precipitate started to form. After two hours the mixture was filtered and the solid which was washed with anhydrous ethyl ether, melted at 191°-193°. The solid showed peaks by nuclear magnetic resonance spectroscopy at 4.0 ppm and 3.8 ppm for the methoxy groups, 6.0 ppm for the H of pyrimidine and 7.6 ppm for the hydrogens on thiophene. The infrared absorption spectrum showed absorption peaks at 1730 and 1700 cm-1 consistent for the two carbonyl peaks in the desired product.

Aufarbeitung

  1. dissolutionAll of the solid reactant dissolved and after twenty minutes
  2. stirringof stirring a precipitate
  3. customto form
  4. filtrationAfter two hours the mixture was filtered
  5. washthe solid which was washed with anhydrous ethyl ether, melted at 191°-193°
  6. customThe infrared absorption spectrum
  7. customabsorption peaks at 1730 and 1700 cm-1 consistent for the two carbonyl peaks in the desired product

Quellen und Nachweise

ORD-Eintrag
ord-11f3d1b656764759a62299f35e155c3e
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04701535

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