Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | HCID 86675959 | HCID 86675959 | — |
| Reactant | HCID 178418816 | HCID 178418816 | — |
| Catalyst | Ferric acetylacetonate | HCID 5483663 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71186280 | HCID 71186280 | 51% |
Reaction Steps
Under argon and at 0° C., 2.0 ml of a 2.0 M solution of isobutylmagnesium bromide in tetrahydrofuran were slowly added dropwise to a degassed solution of 1.50 g of 7-chloro-5-(4-chlorobenzyl)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-d]pyrimidine and 65 mg of iron(III) acetylacetonate in 20 ml of dry tetrahydrofuran. After 15 min at 0° C., diethyl ether was added to the reaction mixture, and 10% strength aqueous citric acid solution was added with ice cooling. The phases were separated, and the aqueous phase was extracted twice with diethyl ether. The combined organic phases was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. From the crude product, 0.80 g (51%) of the title compound was isolated after reprecipitation from acetonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321787B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-db3ce5c3def84491bdc828864e38e6d7 |
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| Source note | uspto-grants-2016_04 |
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