Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | Sodium Ascorbate | HCID 23667548 | — |
| Reactant | HCID 178514591 | HCID 178514591 | — |
| Catalyst | Copper Sulfate | HCID 24462 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178458781 | HCID 178458781 | 34.4% |
Reaction Steps
1-[trans-4-(Azidomethyl)cyclohexyl]-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine (30.0 mg, 0.101 mmol) and 2-methyl-3-butyn-2-ol (12.0 μL, 0.122 mmol) in dichloromethane (3 mL) were mixed with copper(II) sulfate (24.0 mg, 0.152 mmol) and sodium ascorbate (60.0 mg, 0.304 mmol) and then stirred at 80° C. for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→0/1-ethyl acetate/methanol=20/1 (v/v)) to give the title compound as a colorless solid (13.2 mg, yield 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09216999B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-f92711c7c0fb48a99c378f58702f95d9 |
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| Source note | uspto-grants-2015_12 |
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