HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → tert-butyl 4-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-methyl-1H-pyrazol-4-amine | HCID 17354268 | — |
| Reactant | Tert-butyl 4-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.4]nonane-2-carboxylate | HCID 118390003 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | tert-butyl 4-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate | HCID 118390050 | 55.3% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
To a suspension of tert-butyl 4-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (0.34 g, 0.93 mmol) in n-BuOH (5.0 mL) was added 1-methyl-1H-pyrazol-4-amine hydrochloride (0.25 g, 1.85 mmol) and DIPEA (0.48 g, 3.71 mmol). The mixture was stirred in a sealed tube and heated to 150° C. overnight, then concentrated in vacuo. The residue was purified by silica gel column chromatography (EA) to give the product as a yellow solid (0.22 g, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-d1dd1f1e34f24995a05388cab058c83f |
| Source note | uspto-grants-2016_08 |