HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)(cyclopropyl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidine-4-carbonitrile | HCID 131736016 | — |
| Reactant | HCID 178418630 | HCID 178418630 | — |
| Product | (6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)(cyclopropyl)methanone | HCID 131736018 | — |
Reaction Steps
Under a nitrogen atmosphere, to a solution of 6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidine-4-carbonitrile (11.3 g) in THF (100 mL) was added 0.70 M cyclopropylmagnesium bromide (86 mL) at 0° C., and the mixture was directly stirred for 30 min. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as a brown oil. This compound was used for the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382188B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-7617a588e7334074beae765eccf7d4e1 |
| Source note | uspto-grants-2016_07 |