HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-chloro-N2-(1-methyl-1H-imidazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | tert-butyl 5-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate | HCID 118390059 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-chloro-N2-(1-methyl-1H-imidazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine | HCID 118389989 | 95% |
Reaction Steps
To a solution of tert-butyl 5-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (398.3 mg, 0.92 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (10 mL, 40 mmol). The reaction mixture was stirred at rt for 1 h and concentrated in vacuo. The residue was dissolved in water (30 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the title compound as a beige solid (0.29 mg, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-7064f4fe36ca4bd8be364135cea36283 |
| Source note | uspto-grants-2016_08 |