HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-((5-Chloro-4-(methylamino)pyrimidin-2-yl)amino)-3-(difluoromethoxy)benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Methyl 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoate | HCID 58539120 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-((5-Chloro-4-(methylamino)pyrimidin-2-yl)amino)-3-(difluoromethoxy)benzoic acid | HCID 58539125 | 52% |
Reaction Steps
Methyl 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoate (500 mg) was dissolved in 5 mL of THF and 5 mL of water. After dissolution, 234 mg of lithium hydroxide was added and the reaction was stirred at room temperature over night. The mixture was checked by LCMS and then carefully acidified with 1N HCl and partitioned with ethyl acetate. The organic layer was concentrated and purified by silica gel chromatography to give 250 mg of 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08802674B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-1b8455a556d34d2ab1035d77c7270a47 |
| Source note | uspto-grants-2014_08 |