Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Reactant | 5-Bromo-6-methylpyridin-3-amine | HCID 18458896 | — |
| Reactant | HCID 178418936 | HCID 178418936 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 89536594 | HCID 89536594 | — |
| Product | HCID 89536837 | HCID 89536837 | — |
Reaction Steps
1,2,3-Triazole (45 mg), cesium carbonate (260 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (76 mg), and copper iodide (50 mg) were added to a DMAc (2 ml) solution containing 5-bromo-6-methylpyridin-3-amine (100 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 110° C. for 8 hours. The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate and washing with saturated saline. The organic layers were dried over anhydrous sodium sulfate. Next, the solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 20:1). A white solid of 6-methyl-5-(2H-1,2,3-triazol-2-yl)pyridin-3-amine (12.8 mg) and brown oily matter of 6-methyl-5-(1H-1,2,3-triazol-1-yl)pyridin-3-amine (6.7 mg) were thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051310B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-b4eb451a27c546479d76d6a86b6bf715 |
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| Source note | uspto-grants-2015_06 |
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