Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Chloro-5-methyl-6-(trifluoromethyl)pyrimidine | HCID 17856518 | — |
| Reactant | 1H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)- | HCID 67111459 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86673377 | HCID 86673377 | 91.4% |
Reaction Steps
1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 100 mg, 0.465 mmol), 4-chloro-5-methyl-6-(trifluoromethyl)pyrimidine (ANICHEM CAS425394-59-8, 83 mg, 0.465 mmol) and triethylamine (0.130 mL, 0.929 mmol) were added together in N,N-dimethylformamide (5 mL) and the resulting mixture was stirred at room temperature for overnight. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by trituration in diethyl ether. The resulting solid was dissolved in 1:1 ethyl acetate:methanol and 4M HCl in 1,4-dioxane was added. The mixture was then evaporated under reduced pressure, the resulting residue was triturated again in diethyl ether the mixture was allowed to cool to room temperature and the white solid was collected to give the titled compound as a white solid (175 mgs);
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796283B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-a25f2c00359b4edfa24d410df38d90f1 |
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| Source note | uspto-grants-2014_08 |
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