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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 872097Generated: October 30, 2026

Pyridine → 5-Chloro-7-(3,5-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine

https://huagongshe.com/reaction/872097

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantPhosphorus oxychlorideHCID 24813—
Reactant7-(3,5-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneHCID 136393908—
Product5-Chloro-7-(3,5-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidineHCID 86688005—

Reaction Conditions

Temperature100 °C

Reaction Steps

7-(3,5-Difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one (521 mg) is dissolved in POCl3 (15 mL) and pyridine (0.2 mL) and stirred overnight while heating at 100° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with 1 M NaHCO3 aqueous solution and brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield the target compound (327 mg). 1H NMR (CDCl3, 300 MHz) δ 7.63 (m, 2H), 7.02 (m, 1H), 6.82 (m, 1H), 6.52 (m, 1H), 2.52 (s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975264B2
Source datasetuspto-grants-2015_03
ORD IDord-7e2118b5f89f4503aa5924b5603874c1
Source noteuspto-grants-2015_03