Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromopyrimidine | HCID 78345 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 89523946 | HCID 89523946 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 71555128 | HCID 71555128 | 25.5% |
Reaction Steps
To a solution of rac-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylic acid 2,4-dichloro-benzylamide (150 mg, 270 μmol) in toluene (6 mL) were added 2-bromopyrimidine (43 mg, 270 μmol) and triethylamine (27 mg, 270 μmol). After addition of tris(dibenzylideneacetone)dipalladium(0) (5 mg, 5 μmol), BINAP (10 mg, 16 μmol) and potassium tert-butylate (30 mg, 270 μmol) the reaction mixture was heated under an argon atmosphere to 110° C. for 20 h. It was filtered and concentrated in vacuo. Purification by chromatography (SiO2; dichloromethane:methanol 1:0 to 9:1) afforded the title compound (26 mg, 25%) as a white solid. MS (EI) m/e: 378.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09139593B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-6e559ee3ad8340a7b4ea4583d845bd4d |
|---|
| Source note | uspto-grants-2015_09 |
|---|
