Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Chloroform methanol | HCID 21584188 | — |
| Reactant | HCID 86724354 | HCID 86724354 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86724353 | HCID 86724353 | 78.5% |
Reaction Steps
To a solution of 3-((3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)amino)-2-hydroxy-3-oxopropyl methanesulfonate (0.240 g) in THF was added NaH (0.018 g) and the reaction mixture was stirred at room temperature for 30 min. The reaction was monitored on TLC using CHCl3:methanol (9:1) as mobile phase. After completion, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by Combiflash, and the product eluted with 1.6% methanol in CHCl3 to give 0.16 g of N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09415049B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-cfa93eb5167240fcadd04856ab72b0d3 |
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| Source note | uspto-grants-2016_08 |
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