Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 54588903 | HCID 54588903 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67446055 | HCID 67446055 | 78.4% |
Reaction Steps
To (6-bromo-pyridin-3-yl)-[5-(4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-6-fluoro-pyridin-2-yl]-amine (P-4020, 0.040 g, 0.090 mmol) in 5.0 mL of tetrahydrofuran under nitrogen at −78° C., tert-butyllithium (0.531 mL, 1.70 M in hexane, 0.903 mmol) is added. The reaction is stirred at −78° C. for 30 minutes, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified with silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-4021, 25.7 mg). MS (ESI) [M+H+]+=364.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901118B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-6e1b547e42544a679fd07d65ded9d7ce |
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| Source note | uspto-grants-2014_12 |
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