Tetrahydro-4H-pyran-4-ol → 7-Benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one

Temperature

5 °C

Di-tert-butyl azodicarboxylate (16.3 g) was added portionwise to a stirred mixture of 7-benzyloxy-5-hydroxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (17 g), 4-hydroxytetrahydropyran (5.4 g) and methylene chloride (200 ml) that had been cooled to 5° C. The mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The mixture was evaporated and the residue was dissolved in a saturated methanolic ammonia solution. The resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The solid so obtained was dried under vaccuum to give 7-benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one (12.5 g); NMR Spectrum: (DMSOd6) 1.6–1.7 (m, 2H), 1.85–1.95 (m, 2H), 3.5 (m, 2H), 3.9 (m, 2H), 4.75 (m, 1H), 5.22 (s, 2H), 6.7 (d, 1H), 6.8 (d, 1H), 7.3–7.5 (m, 5H), 7.9 (s, 1H); Mass Spectrum: M+H+ 353.

1. temperatureto warm to ambient temperature
2. customThe mixture was evaporated
3. dissolutionthe residue was dissolved in a saturated methanolic ammonia solution
4. stirringThe resultant mixture was stirred at ambient temperature for 16 hours
5. customThe mixture was evaporated
6. customthe residue was triturated under diethyl ether
7. customThe solid so obtained
8. customwas dried under vaccuum

ORD record

ord-785db5eefdad4038ab4585be386fbdae

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049438B2