HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-(methylsulfonyl)-3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine | HCID 118390069 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-(methylsulfonyl)-3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine | HCID 118389997 | 72% |
Reaction Steps
To a suspension of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (0.16 g, 0.43 mmol) in anhydrous DCM (10.0 mL) were added DMAP (0.011 g, 0.092 mmol) and Et3N (0.15 mL, 1.10 mmol), followed by methanesulfonyl chloride (0.076 g, 0.66 mmol) at 0° C. The mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a light yellow solid (0.14 g, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-96fb8b7ee552400e9133085e0f021af6 |
| Source note | uspto-grants-2016_08 |