HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-((1-methyl-1H-pyrazol-4-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate | HCID 118390115 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-((1-methyl-1H-pyrazol-4-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrile | HCID 118390027 | 57.02% |
Reaction Steps
To a solution of tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (425 mg, 1.001 mmol) in dichloromethane (30 mL) was added the solution of HCl in EtOAc (10 mL, 40 mmol), and the mixture was stirred at rt for 1 h. The mixture was diluted with water (20 mL) and adjust to pH=8-9 with saturated NaHCO3 solution and then extracted with DCM (30 mL×3). The combined organic phases were washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=5/1) to give the title product as a white solid (185.2 mg, 57.02%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-6d32903c239d4b258ece03304adf5a69 |
| Source note | uspto-grants-2016_08 |