HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → (S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-bromo-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | HCID 58396041 | — |
| Reactant | (S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one | HCID 90102580 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | (S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one | HCID 131736122 | 38% |
Reaction Steps
(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (330 mg, 1.08 mmol) was treated with 5-bromo-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (430 mg, 1.19 mmol), cesium fluoride (33 mg, 0.22 mmol), N,N-diisopropylethylamine (1.1 mL, 6.49 mol) and 1-butanol according to Preparation 13. The residue was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) to give 0.24 g (38% yield) of the title compound. Purity 100%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-3f01e8584c3b4e0a8d8ca7b2b6ac4e5e |
| Source note | uspto-grants-2016_07 |