Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Iodine | HCID 807 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | 1-[4-(6-Aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea | HCID 23155080 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23155066 | HCID 23155066 | 63.2% |
Reaction Steps
In 18 mL of tetrahydrofuran, 300 mg (0.67 mmol) of 1-[4-(6-aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea was suspended, and the suspension was cooled to −70° C. To the suspension, 3 mL of a tetrahydrofuran solution of lithium diisopropylamide (1.8 M) was added dropwise, and with stirring the temperature of the suspension was raised to 0° C. over two hours. Again, the suspension was cooled to −70° C., and 350 mg (1.38 mmol) of iodine was added thereto, and the suspension was stirred one hour. To the reaction solution, 100 μL of acetic acid was added, and the reaction solution was concentrated, and purified by a silica gel column (dichloromethane:methanol=9:1) to obtain 243 mg (63%) of a target product as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609656B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-3c82fac23844497ba66f6917192f4f31 |
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| Source note | uspto-grants-2013_12 |
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