Triphenylphosphine → Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylate

To a solution of triphenylphosphine (2 eq) in THF was added di-terbutylazodicarboxylate (2 eq). The mixture was stirred 15 minutes at ambient temperature under nitrogen atmosphere. To that was added tert-butyl-4-hydroxypiperidine-1-carboxylate (5 eq). The mixture was stirred 15 minutes at ambient temperature followed by addition of 2-(ethylthio) quinazolin-7-ol (1 eq). The mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated and purified by flash column chromatography (10% EtOAc/Hexane) to provide product as a white solid in 90% yield. ES/MS m/z 390.1 (MH+).

1. stirringThe mixture was stirred 15 minutes at ambient temperature
2. stirringThe mixture was stirred overnight at ambient temperature
3. concentrationThe reaction mixture was concentrated
4. custompurified by flash column chromatography (10% EtOAc/Hexane)
5. customto provide product as a white solid in 90% yield

ORD record

ord-ce4eee9a0cee4e84bfbff6469135e045

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932262B2