Water → 5-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Quinazolin-4-ol (1.0 g, 6.84 mmol) was dissolved in DMF (7 mL). Cs2CO3 (2.23 g, 6.84 mmol) was added at RT and the mixture was stirred for 10 min. A solution of 5-(5-bromo-pentyloxy)-2-hydroxymethyl-pyran-4-one 10 (1.90 g, 6.52 mmol) in DMF (7 mL) was added via syringe. This mixture was stirred at 50° C. for 2 h. Water (150 mL) was added and the mixture extracted with EtOAc (2×100 mL), washed with water (3×100 mL), brine (3×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=95:5. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 15 was obtained (0.61 g, 26% yield) as a pale yellow solid.

1. stirringThis mixture was stirred at 50° C. for 2 h
2. extractionthe mixture extracted with EtOAc (2×100 mL)
3. washwashed with water (3×100 mL), brine (3×100 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

ORD 기록

ord-ec877a2919ae4c9ca88a301d964f4269

출처 데이터셋

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07514432B2