HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N2-(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)-5-methyl-N4-(7-fluoro-1H-indol-4-yl)pyrimidine-2,4-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 4-Bromo-7-fluoroindole | HCID 3822541 | — |
| Reactant | 5-Methyl-N2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine | HCID 57675085 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N2-(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)-5-methyl-N4-(7-fluoro-1H-indol-4-yl)pyrimidine-2,4-diamine | HCID 44816273 | 1.7% |
Reaction Steps
A mixture of intermediate 38 (413 mg, 1.3 mmol), 4-bromo-7-fluoro-1H-indole (310 mg, 1.45 mmol), Pd2(dba)3 (92 mg, 0.1 mmol). Xantphos (180 mg, 0.3 mmol) and cesium carbonate (1.3 g, 4 mmol) was suspended in dioxane (50 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by HPLC to afford the title compound (10 mg of HCl salt, 1.5%) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08133900B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-f8c8500a32c340eeb6fb58a3a23e7f68 |
| Source note | uspto-grants-2012_03 |