Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,3-Dihydro-1,4-benzodioxin-6-ol | HCID 9115273 | — |
| Reactant | N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine | HCID 57708264 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 57708304 | HCID 57708304 | 29% |
Reaction Steps
A stirred mixture of 2,3-dihydrobenzo[b][1,4]dioxin-6-ol (0.137 g, 0.90 mmol), Cs2CO3 (0.734 g, 2.25 mmol), CuI (0.02 g, 10% w/w), and N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine (0.29 g, 0.90 mmol) in NMP (1 mL) was heated at 100° C. for 16 h. The reaction mixture was cooled to rt and slowly added to demineralised water. The solid that precipitated was collected by filtration and was further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate, 7/3) to give N2-(6-(2,3-dihydrobenzo[b][1,4]dioxin-6-yloxy)pyrimidin-4-yl)pyridine-2,6-diamine (0.088 g, 29%) as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09296704B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-5c59e16199a340dd9b4d47bf1c2a29c6 |
|---|
| Source note | uspto-grants-2016_03 |
|---|
