Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine | HCID 68753485 | — |
| Reactant | 4-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde | HCID 86703051 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 178424651 | HCID 178424651 | — |
Reaction Steps
164.5 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 4.8 mL NMP. After addition of 0.2 mL triethylamine the reaction mixture is stirred for one hour. 200 mg (0.57 mmol) 4-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.06 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 207.4 mg (0.98 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for another night. The reaction mixture is poured on saturated NaHCO3/ice water. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 92.2 mg (27.9%) of the desired product are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957064B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-ba8518b055fb4d2d8f5039e5b769382f |
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| Source note | uspto-grants-2015_02 |
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