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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2416847Generated: November 1, 2026

Triethylamine → [1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/2416847

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactanttert-butyl N-(pyrrolidin-3-yl)carbamateHCID 2757234—
Reactant3-Benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dioneHCID 22632889—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product[1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl esterHCID 5698962046.6%

Reaction Conditions

Temperature70 °C

Reaction Steps

A solution of 3-benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione (Example E-3, 0.15 g, 0.42 mmol) in DMF (3.0 mL) was reacted with pyrrolidin-3-yl-carbamic acid tert-butyl ester (0.700 g, 3.5 mmol) and triethylamine (0.70 mL, 5.0 mmol) then heated to 70° C. overnight. The mixture was then cooled, diluted with H2O, and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.10 g of the title compound as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06825199B2
Source datasetuspto-grants-2004_11
ORD IDord-c4f7c640cb0c4ed9869089afe9a61879
Source noteuspto-grants-2004_11