Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(2-Amino-6-chloropyrimidin-4-yl)-N-(tert-butoxycarbonyl)-L-phenylalanine | HCID 25191339 | — |
| Reactant | 1-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol | HCID 61644635 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66743048 | HCID 66743048 | 82.6% |
Reaction Steps
Cs2CO3 (8.45 g, 26 mmol) was added to the solution of 1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanol (1.4 g, 5.2 mmol) in 10 ml of anhydrous 1,4-dioxane, the mixture was stirred for 5 minutes, then (S)-3-[4-(2-amino-6-chloro-pyrimidin-4-yl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (2.0 g, 5 mmol) was added, and the resulting mixture was heated at 110° C. overnight. After cooling, 5 ml of water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 2.6 g of (S)-3-(4-{2-amino-6-[1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethoxy]-pyrimidin-4-yl}phenyl)2tertbutoxycarbonylamino-propionic acid (yield: 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968559B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-a414f6763e4341a0a42392b5edc63b3a |
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| Source note | uspto-grants-2011_06 |
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