Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromo-2-methyl-1-propene | HCID 357785 | — |
| Reactant | HCID 67216733 | HCID 67216733 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58382377 | HCID 58382377 | 106% |
Reaction Steps
tert-Butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.50 g, 0.95 mmol) and Cs2CO3 (1.55 g, 4.75 mmol) were combined in DMF (19 mL). 3-Bromo-2-methylpropene (0.191 mL, 1.90 mmol) was added and the mixture was heated at about 65° C. for about 3 h. EtOAc (50 mL) and water (50 mL) were added and the layers separated. The organic layer was washed with 5% aqueous LiCl (3×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl(2-methylallyl)carbamate (0.584 g, 106%): LC/MS (Table 2, Method h) Rt=2.43 min.; MS m/z: 581 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785639B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-4e77d918e4b541f69e4ef10f348ab1b0 |
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| Source note | uspto-grants-2014_07 |
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