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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851269Generated: October 31, 2026

Sodium triacetoxyborohydride → 6-phenyl-5-{4-[4-(6-trifluoromethyl-1H-benzimidazol-2-yl)piperidin-1-ylmethyl]-phenyl}-pyrazolo[1,5-a]pyrimidine

https://huagongshe.com/reaction/1851269

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant2-Piperidine-4-yl-6-trifluoromethyl-1h-benzimidazole hydrochloride saltHCID 68752934—
Reactant4-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehydeHCID 86630665—
Product6-phenyl-5-{4-[4-(6-trifluoromethyl-1H-benzimidazol-2-yl)piperidin-1-ylmethyl]-phenyl}-pyrazolo[1,5-a]pyrimidineHCID 6875461144.8%

Reaction Steps

250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 308 mg (1 mmol) 2-piperidine-4-yl-6-trifluoromethyl-1H-benzimidazole hydrochloride salt were treated as previously described. Additional NaBH(OAc)3 has been added after one, two and three hours (two equivalents each). After a further hour stirring at room temperature additional 31 mg 2-piperidine-4-yl-6-trifluoromethyl-1H-benzimidazole hydrochloride salt and two equivalents NaBH(OAc)3 were added. After stirring overnight and two further additions of NaBH(OAc)3 the solvents were evaporated. Workup and purification yields 208 mg of the desired compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957064B2
Source datasetuspto-grants-2015_02
ORD IDord-5f4e87defabc4e5fa29acd39a04d847d
Source noteuspto-grants-2015_02