HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-Methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Amino-2-hydroxytoluene | HCID 76081 | — |
| Reactant | 4-(2-Chloropyridin-3-yl)pyrimidine | HCID 16108974 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 3-Methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine | HCID 58397198 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To 4-amino-2-methyl-phenol (193 mg, 1.57 mmol) was added Cs2CO3 (1.02 g, 3.14 mmol) and NMP (2.0 mL). The mixture was heated for 5 minutes at 100° C., cooled to RT and 4-(2-chloro-pyridin-3-yl)-pyrimidine (300 mg, 1.57 mmol) was added. The mixture was heated in the microwave to 210° C. for 20 minutes, cooled, filtered through a plug of cotton and purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield 3-methyl-4-(3-pyrimidin-4-yl-pyridin-2-yloxy)-phenylamine. MS m/z=279 [M+1]+. Calc'd for C16H14N4O: 278.32.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07880000B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-814d9bbf2ef44322897a8362d081c8fe |
| Source note | uspto-grants-2011_02 |