Buchwald–Hartwig amination: 1-(6-Chloropyrimidin-4-yl)benzimidazole → 6-(benzimidazol-1-yl)-N-[5-[[(2R)-1-methylpyrrolidin-2-yl]methoxy]-2-pyridinyl]pyrimidin-4-amine
14% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 1-(6-Chloropyrimidin-4-yl)benzimidazole | C₁₁H₇ClN₄ | |
| Reactant | CN1CCC[C@@H]1COc1ccc(N)nc1 | C₁₁H₁₇N₃O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 6-(benzimidazol-1-yl)-N-[5-[[(2R)-1-methylpyrrolidin-2-yl]methoxy]-2-pyridinyl]pyrimidin-4-amine | C₂₂H₂₃N₇O | 14.09% |
Conditions
- Temperature
- 100 °C
Yield
- 14% of 6-(benzimidazol-1-yl)-N-[5-[[(2R)-1-methylpyrrolidin-2-yl]methoxy]-2-pyridinyl]pyrimidin-4-amine.
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (31.6 mg, 0.03 mmol) was added to (R)-5-((1-methylpyrrolidin-2-yl)methoxy)pyridin-2-amine (143 mg, 0.69 mmol), 1-(6-chloropyrimidin-4-yl)-1H-benzo[d]imidazole (159 mg, 0.69 mmol), sodium t-butoxide (99 mg, 1.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (59.8 mg, 0.10 mmol) in toluene (6 mL) at 20°C under nitrogen. The resulting suspension was stirred at 100 °C for 16 hours then cooled to room temperature. LCMS analysis indicates no SM, product peak present. The reaction mixture was concentrated _in vacuo_. The residue was dissolved in DCM (100 mL) and washed with water (100 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was purified by flash si
The source
This record comes from experimental reaction archive (ord-2784ae4fbb2641c38c53b79f14f3e80f). Open the source and check it against what is on this page.
experimental reaction archive record ord-2784ae4fbb2641c38c53b79f14f3e80f from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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