HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → N-(4-chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)pyrimidin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Methylpent-3-en-2-ol | HCID 138190 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Reactant | 2-Chloro-5-(pyrimidin-2-ylamino)phenol | HCID 59474945 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(4-chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)pyrimidin-2-amine | HCID 86645050 | 17% |
Reaction Steps
To a flask was added 2-chloro-5-(pyrimidin-2-ylamino)phenol (50 mg, 0.23 mmol), 4-methylpent-3-en-2-ol (23 mg, 0.23 mmol), Ph3P (59 mg, 0.23 mmol) and THF (0.08 mL). The reaction vessel was lowered into a sonication bath and sonicated for several minutes giving a clear and highly viscous solution. While sonication, DEAD (0.044 mL, 0.23 mmol) was added. After 1 h, the reaction mixture was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel (hexane:EtOAc 7/3) to give the product in 17% yield (12 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018209B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-386f609eef8240f0abaae02365669c25 |
| Source note | uspto-grants-2015_04 |