Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | HCID 66739651 | HCID 66739651 | — |
| Reactant | (5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine | HCID 86664780 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 46944956 | HCID 46944956 | — |
Reaction Steps
To a 2 mL microwave vessel was charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.043 mmol, 23.5 mg), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (0.047 mmol), K3PO4 (130 mmol, 27 mg), and PdCl2(dppf).CH2Cl2 (0.0043 mmol, 3.5 mg). To this mixture was added 9:1 dioxane:H2O (1 mL). The vessel was flushed with argon and heated to 160° C. for 30 minutes in microwave synthesizer. Upon completion, the reaction was concentrated in vacuo and the residue was dissolved in 1 mL TFA. This reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield 5-(4-(1H-pyrazol-4-yl)cyclohex-1-enyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as yellow solid. (m+H=408.30, retention time=3.16 min)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-34ac0394602e46478a6bf8cb9790801c |
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| Source note | uspto-grants-2013_11 |
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