Pyrrolidine → 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((pyrrolidin-1-yl)methyl)-4H-pyran-4-one

Methanesulfonic acid 4-oxo-5-[5-(quinazolin-4-yloxy)-pentyloxy]-4H-pyran-2-ylmethyl ester 20 (100 mg, 0.23 mmol) was dissolved in dichloromethane (3 mL). Pyrrolidine (48 μL, 0.575 mmol) was added via syringe. The mixture was stirred at 45° C. for 1.5 h. .CH2Cl2 (75 ml) was added and the solution was washed with NaHCO3 10% (3×50 mL), brine (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=90:10. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((pyrrolidin-1-yl)methyl)-4H-pyran-4-one EHT 5317 was obtained (30 mg, 35% yield) as a colourless oil.

1. washthe solution was washed with NaHCO3 10% (3×50 mL), brine (3×50 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. customevaporated
5. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

ORD-Eintrag

ord-36d296f61eac49cebe1b2291f4a261c1

Quelldatensatz

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07514432B2