Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate | HCID 235097 | — |
| Reactant | HCID 58972439 | HCID 58972439 | — |
| Reactant | HCID 68779108 | HCID 68779108 | — |
| Reactant | HCID 68779156 | HCID 68779156 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58972459 | HCID 58972459 | — |
Reaction Steps
The title compound was prepared in analogy to the synthesis of 4-(5-cyanomethoxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (intermediate C32/step 1) from 4-(5-hydroxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (intermediate C31/step 2) by reaction with rac-toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (commercially available) and potassium carbonate in DMF at rt for 48 h, followed by BOC and isopropylidene cleavage with 4 M HCl in dioxane and ethanol at 60° C. in analogy to the procedure described for 2-[4-methoxy-6-(piperidin-4-ylamino)-[1,3,5]triazin-2-ylamino]-ethanol (intermediate C26/step 3) and subsequent ion exchange chromatography on Q-Sepharose Fast Flow. MS (ISP): 269.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07855194B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-0b17bad8f7e5471f81cb55f3ff280d2f |
|---|
| Source note | uspto-grants-2010_12 |
|---|
