HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dioxane → 4-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | [4-(5-Bromo-pyrimidin-2-ylamino)-phenyl]-methanol | HCID 57632949 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Catalyst | HCID 178418406 | HCID 178418406 | — |
| Product | 4-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde | HCID 57632695 | — |
Reaction Conditions
| Temperature | 130 °C |
|---|
Reaction Steps
To a solution of [4-(5-bromo-pyrimidin-2-ylamino)-phenyl]-methanol 15 (0.94 mmol) in dioxane (2 mL) is added manganese (IV) oxide (4.7 mmol) and TBAI (0.06 mmol). The reaction mixture is heated in a microwave oven at 130° C. for 30 min. Purification by silica gel chromatography using hexane:EtOAc=1:1 affords 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde 16. 1H NMR (400 MHz, d6-DMSO) δ 10.45 (s, 1H), 9.85 (s, 1H), 8.72 (s, 2H), 7.96 (d, J=8.4 Hz, 2H), 7.85 (d, J=8.4 Hz, 2H). MS (m/z) (M+1)+: 278.0, 280.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293757B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-5a85d17efe1b4383960d9750713ce464 |
| Source note | uspto-grants-2012_10 |