Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 57516772 | HCID 57516772 | — |
| Reactant | HCID 90038660 | HCID 90038660 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 123832164 | HCID 123832164 | 56.4% |
Reaction Steps
In a 10 mL pyrex tube, 2-bromo-5-(phenylethynyl)pyrimidine (CAS: 1338493-52-9)(80 mg, 309 μmol, Eq: 1.00) and (rac)-(3aRS,6aSR)-1-(3-Methoxy-propyl)-hexahydro-cyclopentaimidazol-2-one (68.0 mg, 309 μmol, 1.0 equiv.) were dissolved in 2 ml of Toluene. Cesium carbonate (201 mg, 618 μmol, 2.0 equiv.), Xanthphos (7.15 mg, 12.4 μmol, 0.04 equiv.) and Pd2(dba)3 (5.65 mg, 6.18 μmol, 0.02 equiv.) were added and the red-brown reaction mixture was stirred at 90° C. for 3 hr. The reaction mixture was filtered, adsorbed on silica, and purified by flash chromatography (silica gel, 20 g with 1 g Silica-NH2, 30% to 100% EtOAc in heptane gradient at 301 nm). One obtained 65.6 mg of the title compound as a yellow oil; MS: m/e=377.6 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09199971B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-6f32f9b859864822b6b07a6be8c26860 |
|---|
| Source note | uspto-grants-2015_12 |
|---|
