HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dioxane → HCID 67295403, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734620 | — |
| Reactant | HCID 86673505 | HCID 86673505 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67295403 | HCID 67295403 | 49% |
Reaction Steps
A mixture of 4-(2-chloro-5-(methylthio)pyrimidin-4-yl)morpholine (0.3 g, 1.22 mmole), 4-aminophenylboronic acid pinacol ester (0.58 g, 2.68 mmole), sodium bicarbonate (0.28 g, 2.68 mmole), Pd(PPh3)4 (0.14 g, 0.122 mmole), dioxane (15 ml) and H2O (3.5 ml) was heated to reflux. After 12 hrs, the reaction mixture was cooled, diluted with EA, washed with brine, and dried (MgSO4), and the solvent was removed in vacuo. Purification on silica gel (EA/Hex=1/2) yielded the desired compound (180 mg, 49%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09315491B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-395b9f37c586456b81e14638587e397a |
| Source note | uspto-grants-2016_04 |