4-Aminopyridine → 2-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

Temperatur

20 °C

A mixture of the product of Example 7, 6-(3,5-dimethoxy-phenyl)-8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.280 g, 10.75 mmol), and 4-aminopyridine (0.5 g, 15.3 mmol) was placed in a small round bottom flask and immersed in an oil bath at 180° C. for 5 minutes with stirring. The reaction mixture was cooled to 20° C. and the mixture triturated with water (10 mL). The insoluble product was filtered and dried in air on the filter. The crude product was purified by column chromatography eluting with a solvent gradient starting with pure chloroform and finishing with methanol/chloroform (1:20). The product was crystallized by suspending it in methanol (10 mL) and adding methylene chloride (30 mL) until a solution resulted. The solution was concentrated on a steam bath to approximately 8 mL in volume. The precipitated product was filtered and washed with methanol (0.5 mL) to afford 112 mg of the titled compound. mp 305–307° C.

1. customwas placed in a small round bottom flask
2. customthe mixture triturated with water (10 mL)
3. filtrationThe insoluble product was filtered
4. customdried in air on the filter
5. customThe crude product was purified by column chromatography
6. washeluting with a solvent gradient
7. customThe product was crystallized
8. additionadding methylene chloride (30 mL) until a solution
9. customresulted
10. concentrationThe solution was concentrated on a steam bath to approximately 8 mL in volume
11. filtrationThe precipitated product was filtered
12. washwashed with methanol (0.5 mL)

ORD-Eintrag

ord-4188f4ac366644778c8fba1cfd6f2e7d

Quelldatensatz

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07022711B2