HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine-2-carbonitrile → 5-methyl-6-phenyl-7-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine-2-carbonitrile | HCID 7522 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate | HCID 22713165 | — |
| Reactant | 4-(5-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde | HCID 86630668 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 5-methyl-6-phenyl-7-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine | HCID 178421909 | — |
Reaction Steps
0.11 ml triethylamine is added to a solution of 105 mg of the product of step 3 in 5 ml methanol. To this solution a solution of 0.122 g 2-(5-Piperidin-[1,2,4]triazol-3-yl)pyridine*2HCl (prepared from tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate and pyridine-2-carbonitrile according to a procedure described in U.S. Pat. No. 4,011,218 or WO2005100344) in 5 ml DMF is added, followed by 0.05 ml glacial acetic acid and 144 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Three additional portions of 2 equivalents NaBH(OAc)3 are added after 2, 4, 6 and 7 hours.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08614218B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-36ccff647c4b44e393149127ee5ab1e1 |
| Source note | uspto-grants-2013_12 |