HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 7-[1-(2-Chloropyrimidin-4-yl)-4-ethoxycarbonylpiperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | 7-(4-Ethoxycarbonylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester | HCID 11155204 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 7-[1-(2-Chloropyrimidin-4-yl)-4-ethoxycarbonylpiperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester | HCID 11410459 | 71.4% |
Reaction Steps
To a solution of 7-(4-ethoxycarbonylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (295 mg) in ethanol (5 ml) were added triethylamine (0.15 ml) and 2,4-dichloropyrimidine (150 mg), and the mixture was stirred under reflux for 1 hour. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) and dried under reduced pressure to give the title compound (263 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06562828B1 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-eb02c0ab21284704b093de9ee3604718 |
| Source note | uspto-grants-2003_05 |