Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | tert-Butyl hydroperoxide | HCID 6410 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | HCID 56851051 | HCID 56851051 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 56851053 | HCID 56851053 | — |
Reaction Steps
A solution of 2-({2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}thio)ethanol (150 mg), titanium tetraisopropoxide (43 μL), methanol (24 μL) and water (10 μL) in dichloromethane was stirred at room temperature for 30 min. 70% Aqueous tert-butyl hydroperoxide solution (0.12 mL) was added to the reaction system, and the mixture was stirred at room temperature for 2 days. An aqueous sodium thiosulfate solution was added to the reaction system, and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=4:1) to give the title compound (118 mg) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07507740B2 |
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| Source dataset | uspto-grants-2009_03 |
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| ORD ID | ord-93b81ce4bf3941fea8de99cbba19a7da |
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| Source note | uspto-grants-2009_03 |
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