HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tert-butyl 3-hydroxyazetidine-1-carboxylate | HCID 2756801 | — |
| Reactant | 4-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine | HCID 68181833 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate | HCID 68181663 | 66.4% |
Reaction Steps
A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1 g, 2.45 mmol), tert-butyl 3-hydroxyazetidine-1-carboxylate (2 g, 11.55 mmol) and cesium carbonate (4 g, 12.28 mmol) in N,N-dimethylformamide (15 mL) was stirred under nitrogen overnight at room temperature. The resulting solution was quenched with 200 mL of water. The precipitate was collected by filtration, washed with 200 mL of water and dried in a vacuum oven to give 750 mg (60%) of tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate as a yellow solid: LC-MS: m/z=+461 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08901313B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-acb10ccff01247a1aec9a8317ff530b6 |
| Source note | uspto-grants-2014_12 |