HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 6-Methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | HCID 68813756 | HCID 68813756 | — |
| Product | 6-Methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine | HCID 11305382 | 51% |
Reaction Steps
A mixture of 2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-6-yl carboxylic acid (Method 43) (1.73 g, 4.0 mmol), methanol (300 ml) and 98% sulphuric acid (1 ml) was heated at reflux for 18 hours. The volatiles were removed by evaporation, the residue dissolved in water and the pH of the resulting solution adjusted to pH 12 with 10M sodium hydroxide. The aqueous solution was extracted with DCM and purified by chromatography on silica gel, eluting with DCM/methanol (100:0 increasing in polarity to 90:10) to give the title compound (904 mg, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07579349B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-522127e1d10e40029bb87a59c930f0f2 |
| Source note | uspto-grants-2009_08 |