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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1052192Generated: October 30, 2026

Hydrogen chloride-ethyl acetate → 2-[(3S)-2-azabicyclo[2.2.2]oct-3-yl]-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

https://huagongshe.com/reaction/1052192

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrogen chloride-ethyl acetateHCID 21866389—
Reactanttert-butyl (3S)-3-[6-(5-methyl-1H-pyrazol-4-yl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]-2-azabicyclo[2.2.2]octane-2-carboxylateHCID 136333934—
SolventMethanolHCID 887—
Product2-[(3S)-2-azabicyclo[2.2.2]oct-3-yl]-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochlorideHCID 136333935—

Reaction Steps

To a solution of tert-butyl(3S)-3-[6-(5-methyl-1H-pyrazol-4-yl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]-2-azabicyclo[2.2.2]octane-2-carboxylate (143 mg) produced in Example 106, step B, in methanol (3.0 mL) was added 4M hydrochloric acid/ethyl acetate solution (1.0 mL) with stirring at room temperature. The reaction system was stirred with heating at 50° C. for 1 hr, and the precipitate was collected by filtration, and washed with ethyl acetate to give the title compound (128 mg) as a colorless solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388195B2
Source datasetuspto-grants-2016_07
ORD IDord-3d03dcca9728474fbbb430b85f39aef8
Source noteuspto-grants-2016_07