HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-bromobutanimide → 4-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 4-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone | HCID 66583804 | — |
| Solvent | Acetonitrile methylene chloride | HCID 21877088 | — |
| Product | 4-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone | HCID 86686663 | 86.9% |
Reaction Steps
To a solution of 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone (128 mg, 0.199 mmol) in CH3CN/DCM (3/1 mL) was added NBS (42.5 mg, 0.239 mmol) and stirred at rt for 30 min. TLC showed complete conversion. All the volatiles were removed under reduced pressure and the residue was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.6 in 20% EtOAc) to afford 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexanone as a pale yellow oil (125 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883801B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-8761742ec5ff43d9bd56ed2b7b05c486 |
| Source note | uspto-grants-2014_11 |