Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Anisole | HCID 7519 | — |
| Reactant | Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](methyl)amino}-2-fluorophenyl)carbamate | HCID 91058342 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 86646079 | HCID 86646079 | 90% |
Reaction Steps
A solution of the above-mentioned crude product of tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](methyl)amino}-2-fluorophenyl)carbamate and anisole (1.5 mL) in trifluoroacetic acid (15 mL) was stirred at 0° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, to the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (638 mg, 90%) as a gray solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08344135B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-574d5d440e734e8ba2090c5239d11d2f |
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| Source note | uspto-grants-2013_01 |
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