Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate | HCID 1514399 | — |
| Reactant | 4-Chloro-7-methoxyquinazolin-6-ol | HCID 23132475 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Quinazoline | HCID 9210 | 48% |
Reaction Steps
Diethyl azodicarboxylate (5.7 ml) was added to 4-chloro-6-hydroxy-7-methoxyquinazoline (4.39 g; prepared as described in Example 1 (Preparation of starting materials)), triphenylphosphine (8.2 g) and (3S)-1-(tert-butoxycarbonyl)-3-hydroxypiperidine (Commercially Available—CAS Registry No 14390044-1) (6.29 g) in dichloromethane (130 ml) and the reaction mixture was stirred at 40° C. for 6 hours. This was allowed to stand overnight at −18° C. then filtered. The filtrates were purified by flash column chromatography eluting with acetone/isohexane/triethylamine (17/82/1) to give 4-chloro-7-methoxy-6-[(3R)-1-(tert-butoxycarbonyl)piperidin-3-yloxy)]quinazoline as a white solid (0.794 g, 48%); Mass Spectrum: (M+H)+394.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07838530B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-7ccba3bb0ccd4944967d345919e33e6d |
|---|
| Source note | uspto-grants-2010_11 |
|---|
