Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 58467880 | HCID 58467880 | — |
| Solvent | Carbon Dioxide | HCID 280 | — |
| Product | HCID 58467857 | HCID 58467857 | 30% |
Reaction Steps
Into a 1-neck round-bottom flask were added {3-[(5-chloro-4-{[(1R)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.26 g, 0.68 mmol) and methylene chloride (5 mL). To the mixture was added a solution of boron tribromide in methylene chloride (3.0 mL, 3.0 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in dry ice when NaHCO3 (saturated aqueous solution, 10 mL) was added. The mixture was allowed to warm up to rt and DCM was added. The aqueous layer was extracted with DCM twice. The organic layers were combined, dried, filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product (40 mg, 30%). LCMS for C19H19BrClN4O (M+H)+: m/z=432.9, 434.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765727B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-15f65832269d4c228c3deb719ab20019 |
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| Source note | uspto-grants-2014_07 |
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