Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-(2-(6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl)-1-ethynyl)-1-cyclopentanol | HCID 9841364 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178479934 | HCID 178479934 | 36% |
Reaction Steps
To 50 mg of 1-{2-[6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethynyl}-1-cyclopentanol were added 3.0 ml of allyl alcohol and 1.0 ml of 5M NaOH, the mixture was stirred at room temperature for 10 minutes, 1.0 ml of THF was added thereto and the mixture was stirred again at room temperature for 15 hours and 40 minutes. The solvent was evaporated and then 200 ml of ethyl acetate and water (1:1) were added and an extraction was carried out. The aqueous layer was extracted with 100 ml of ethyl acetate again and the all organic layers were combined and washed with water and with brine once each. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was purified by a p-TLC (CH2Cl2:MeOH=10:1), the resulting yellowish white crystals were suspended in diethyl ether and the suspension was filtered to give 217 mg of the title compound as white crystals. The yield was 36%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06579868B1 |
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| Source dataset | uspto-grants-2003_06 |
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| ORD ID | ord-9353bf60e72c43cf8ebef2ea5f7d0944 |
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| Source note | uspto-grants-2003_06 |
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