Réaction #343447

ord-11f3d1b656764759a62299f35e155c3e

Équation de réaction

COc1cc(OC)nc(N)n1
2-amino-4,6-dimethoxypyrimidine
COC(=O)c1sccc1S(=O)(=O)N=C=O
2-methoxycarbonyl-3-thiophenesulfonyl isocyanate
COC(=O)c1sccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1
Methyl 3 [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl] aminosulfonyl]-2-thiophenecarboxylate

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.DISSOLUTIONAll of the solid reactant dissolved and after twenty minutes
  2. 2
    workup.STIRRINGof stirring a precipitate
  3. 3
    Autreto form
  4. 4
    FiltrationAfter two hours the mixture was filtered
  5. 5
    Lavagethe solid which was washed with anhydrous ethyl ether, melted at 191°-193°
  6. 6
    AutreThe infrared absorption spectrum
  7. 7
    Autreabsorption peaks at 1730 and 1700 cm-1 consistent for the two carbonyl peaks in the desired product

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04701535uspto-grants-1987_10