Reaktion #3579

Reaktionsgleichung

HCl

potassium hexamethyldisilazane

6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine

6-(2,6-Dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine

ethyl isocyanate

→

title compound

1-[6-(2,6-Dichlorophenyl)-2-(4-diethylamino-butyl-amino)-pyrido[2,3-d]pyrimidin-7-yl]-3-ethyl-urea

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred for an additional 18 hours at ambient temperature
2. 2
   SonstigeThe product was isolated
3. 3
   Filtrationfiltering the resulting solution
4. 4
   Extraktionthe aqueous layer was extracted twice with ethyl acetate
5. 5
   TrocknenThe combined organic extracts were dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate concentrated under vacuum
8. 8
   SonstigeThe product was purified by radial chromatography
9. 9
   Wascheneluting with a solvent mixture of 90:10:1 EtOAC

Vorschrift

To a cooled (5° C.) solution of 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (0.61 g) from Example 53 in THF (6 mL) was added potassium hexamethyldisilazane (0.308 g) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for 30 minutes. Then ethyl isocyanate was added, and the reaction mixture was stirred for an additional 18 hours at ambient temperature. The product was isolated by pouring the reaction mixture into approximately 200 mL of 0.25N aqueous HCl and filtering the resulting solution. The filtrate was made basic with 50% aqueous sodium hydroxide, and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and the filtrate concentrated under vacuum. The product was purified by radial chromatography eluting with a solvent mixture of 90:10:1 EtOAC:MeOH:TEA to afford the title compound.

Quelle