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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 578012Generated: November 1, 2026

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

https://huagongshe.com/reaction/578012

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBarbituric AcidHCID 6211—
Reactant7-Chloro-6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehydeHCID 87369792—
SolventIsopropanolHCID 3776—
Product(2R,4S,4aS)-rel-11-chloro-2,4,8-trimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trioneHCID 67432471—

Reaction Conditions

Temperature85 °C

Reaction Steps

To a solution of 7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehyde (Intermediate 375, 35 mg, 0.119 mmol) in IPA was added barbituric acid (16 mg, 0.113 mmol) and the mixture heated at 85° C. for 16 hours. Solvents were evaporated and the residue thus obtained was purified over silica column using a gradient of methanol in chloroform to give product as a solid. Yield: 10 mg (25%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09040528B2
Source datasetuspto-grants-2015_05
ORD IDord-abe073e5354146d5a3899ee4d9001a7f
Source noteuspto-grants-2015_05