HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 2-Chloro-8-(1-isopropylpiperidin-4-yloxy)quinazoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Isopropylpiperidin-4-ol | HCID 79681 | — |
| Reactant | Di-tert-butyl diazene-1,2-dicarboxylate | HCID 6034084 | — |
| Reactant | 2-Chloro-8-quinazolinol | HCID 59199230 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Chloro-8-(1-isopropylpiperidin-4-yloxy)quinazoline | HCID 59199219 | 88% |
Reaction Steps
To a 0.30M solution of triphenylphosphine (1.5 eq) in THF was added di-tert-butylazodicarboxylate (1.5 eq). The mixture was stirred 15 min at ambient temperature. 4-Hydroxy-1-isopropylpiperidine (4.0 eq) was added. The mixture was stirred 15 min at ambient temperature. 2-Chloroquinazolin-8-ol (1.0 eq) was added. The mixture was stirred an additional 2 h. The crude mixture was concentrated, purified by flash chromatography (EtOAc then 90:10:1 DCM:MeOH:NH4OH), and concentrated to give the desired product in 88% yield. ES/MS m/z 306 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932262B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-6cb201e5246c40fc8dd6d8c4f95e3b75 |
| Source note | uspto-grants-2011_04 |