Isopropanol → 3-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propan-1-ol

Temperatur

100 °C

To a solution of 3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)propan-1-ol (201 mg) synthesized in Example 53 (ii) in isopropyl alcohol (2.5 mL) was added 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (381 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 2.0 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (25 mL), and extracted with ethyl acetate (30 mL×3). The organic layer washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to basic silica gel chromatography (eluent:hexane/ethyl acetate=95/5→20/80). The object fraction was concentrated under reduced pressure and dried. Ethanol/diisopropyl ether (1/9) was added to the residue, and the mixture was stirred with heating to 80° C., allowed to cool to room temperature, and stood still. The resultant precipitate was collected by filtration. The obtained precipitate washed with diisopropyl ether and dried under reduced pressure to give the title compound (375 mg) as white powder crystals.

1. temperatureto cool to room temperature
2. extractionextracted with ethyl acetate (30 mL×3)
3. washThe organic layer washed successively with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. concentrationThe object fraction was concentrated under reduced pressure
7. customdried
8. additionEthanol/diisopropyl ether (1/9) was added to the residue
9. stirringthe mixture was stirred
10. temperaturewith heating to 80° C.
11. temperatureto cool to room temperature
12. filtrationThe resultant precipitate was collected by filtration
13. washThe obtained precipitate washed with diisopropyl ether
14. customdried under reduced pressure

ORD-Eintrag

ord-91aaa449c91348bb929eeb8cd389eff7

Quelldatensatz

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07507740B2