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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851283Generated: October 31, 2026

Triethylamine → HCID 178424651, compound

https://huagongshe.com/reaction/1851283

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 68753485—
Reactant4-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeHCID 86703051—
SolventAcetic AcidHCID 176—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductHCID 178424651HCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957064B2
Source datasetuspto-grants-2015_02
ORD IDord-ba8518b055fb4d2d8f5039e5b769382f
Source noteuspto-grants-2015_02