Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- | HCID 5356682 | — |
| Reactant | HCID 57963172 | HCID 57963172 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57963227 | HCID 57963227 | — |
Reaction Steps
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 0.121 g, 0.790 mmol), (5-fluoro-2-methoxy-pyridin-3-ylmethyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (77), 2.5 mL of N,N-dimethylformamide and cesium carbonate (0.751 g, 2.30 mmol) were combined in a round bottom flask. The reaction was stirred at room temperature for 6 days, then neutralized with 0.1 N aqueous hydrochloric acid, then extracted 3× with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated. The resulting material was purified by silica gel column chromatography, eluting with methanol and dichloromethane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (78, 0.023 g). MS (ESI) [M−H+]−=513.2, 515.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08158636B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-40666c19f0ac44c18347a9c6b377a671 |
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| Source note | uspto-grants-2012_04 |
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