Reacción #2000685

Ecuación de reacción

potassium tert-butoxide

[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methanol

compound

2-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile

water

→

product

2-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]-pyridine-3,5-dicarbonitrile

Disolventes

acetic acid

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to RT
2. 2
   workup.STIRRINGstirred at this temperature for 8 h
3. 3
   OtroA precipitate is formed
4. 4
   Filtraciónwhich was filtered off with suction
5. 5
   OtroThe residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
6. 6
   OtroRemoval of the solvent
7. 7
   Otroon a rotary evaporator

Procedimiento

72 mg (0.64 mmol) of potassium tert-butoxide were suspended in 1 ml of dry dimethoxyethane. 270 mg (1.29 mmol) of [2-(4-chlorophenyl)-1,3-oxazol-4-yl]methanol and 50 mg (0.13 mmol) of the compound from Example 48A were then added in succession. The reaction mixture was stirred at 60° C. for 2 h and then cooled to RT and stirred at this temperature for 8 h. 5 ml of water and 1 ml of 2N acetic acid were added to the reaction mixture. A precipitate is formed, which was filtered off with suction. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gave the product as a solid.

Fuente