Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Methyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazine | HCID 46739039 | — |
| Reactant | HCID 118364736 | HCID 118364736 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 118364802 | HCID 118364802 | 33% |
Reaction Steps
(S)-3-(1-((4-(5-bromopyrimidin-2-yl)morpholine-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile (30 mg, 0.063 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)piperazine (24 mg, 0.094 mmol), Pd(dppf)2Cl2 (2 mg, 0.003 mmol), and Cs2CO3(62 mg, 0.18 mmol) were dissolved in dioxane (4 ml)+H2O (1 ml), and then degassed with N2 (gas), followed by stirring at 80° C. for hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-3-(1-((4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)pyrimidin-2-yl)morpholine-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile (12.1 mg, 33%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09403831B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-705f29104fa34c03bb1ca95c47bca030 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
