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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 245575Generated: October 31, 2026

Barbituric Acid → (2R,4S,4aS)-8-chloro-11-fluoro-2,4-dimethyl-2,4,4a,6-tetrahydro-1H,1'H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'H)-trione

https://huagongshe.com/reaction/245575

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBarbituric AcidHCID 6211—
Reactant3-chloro-6-((2R,6R)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-5-carbaldehydeHCID 86658122—
SolventIsopropanolHCID 3776—
Product(2R,4S,4aS)-8-chloro-11-fluoro-2,4-dimethyl-2,4,4a,6-tetrahydro-1H,1'H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'H)-trioneHCID 6743289326.5%

Reaction Steps

A mixture of 3-chloro-6-((2R,6R)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-5-carbaldehyde (Intermediate 535, 764 mg, 2.44 mmol) and pyrimidine-2,4,6(1H,3H,5H)-trione (313 mg, 2.44 mmol) in iPrOH (3 ml) was heated at reflux for 3 days. Solvent was removed and the residue was recrystallized from methanol. The solids obtained were recrystallized from 1:1 EtOH-Water to afford 273 mg of product consistent with desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08658641B2
Source datasetuspto-grants-2014_02
ORD IDord-69431771947a42c1834895cc325b229a
Source noteuspto-grants-2014_02