Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Pyridinium chloride | HCID 10176127 | — |
| Reactant | 3-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline | HCID 11424434 | — |
| Reactant | HCID 67520938 | HCID 67520938 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57597382 | HCID 57597382 | 40.4% |
Reaction Steps
A mixture of 6-((1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propenyl)-5-ethyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (78 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (61.2 mg), pyridine hydrochloride (26 mg) and phenol (122 mg) was stirred with heating at 120° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with dichloromethane (30 mL), and washed with saturated aqueous sodium hydrogen carbonate (20 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→80:20) to give the title compound (32 mg) as a powder.
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-eb44393fedd44638a22d225f917392a8 |
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| Source note | uspto-grants-2009_03 |
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