Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | D-Proline | HCID 8988 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 24902229 | HCID 24902229 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 71239062 | HCID 71239062 | 43% |
Reaction Steps
4-Chloro-6-(3,4-dichloro-phenyl)-pyrimidine (0.3 g, 1.2 mmol) and D-proline (0.13 g, 1.2 mmol) were added in one portion to a pressure vessel containing a solution of copper (I) Iodide (0.02 g, 0.16 mmol) and potassium carbonate (0.24 g, 1.8 mmol) in DMA (5 ml). The vessel was sealed and heated at 90° C. for 16 hours before being cooled to room temperature. The mixture was cooled to room temperature, diluted with ethyl acetate (10 ml) and acidified to pH 1 with concentrated HCl. The mixture was extracted with ethyl acetate (3×30 ml) and the organic layers were combined, dried (MgSO4), filtered, concentrated and the resulting residue was purified by prep HPLC to give the title compound (0.17 g, 43% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09260422B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-007eaa7693f44da9b46130e3502cbcfe |
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| Source note | uspto-grants-2016_02 |
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