HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl acetate → HCID 59168306, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl acetate | HCID 10908 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Reactant | Lithium dicyclohexylamide | HCID 10932176 | — |
| Reactant | 4-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine | HCID 59168287 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59168306 | HCID 59168306 | — |
Reaction Steps
To lithium dicyclohexyl amide add a solution of acetic acid tert-butyl ester (62 μL, 0.46 mmol) in toluene (2 mL). Stir for 10 min at room temperature, and then add 4-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine (200 mg, 0.38 mmol), Pd2(dba)3 (3.5 mg, 1%) and P(t-bu)3 (0.8 mg, 1%). De-gas the suspension for 5 min and stir for 16 h at room temperature. Dilute with EtOAc, wash with brine, dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify using flash chromatography eluting with EtOAc-Hexanes (1:4) to give the title ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08334382B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-729ce6f6bb3543c8994cbb1124e91e8c |
| Source note | uspto-grants-2012_12 |