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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 732927Generated: October 30, 2026

Water → 1-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-(1-azido-2-bromoethyl)uracil

https://huagongshe.com/reaction/732927

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium AzideHCID 33557—
ReactantN-bromobutanimideHCID 67184—
Reactant1-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-vinyluracilHCID 11091584—
Solvent1,2-DimethoxyethaneHCID 8071—
Product1-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-(1-azido-2-bromoethyl)uracilHCID 1181380881.5%

Reaction Conditions

Temperature0 °C

Reaction Steps

A mixture of 22 (510 mg, 1.14 mmol), saturated solution of sodium azide in water (300 mg, 4.6 mmol), N-bromosuccinimide (223 mg, 1.25 mmol) and 1,2-dimethoxyethane (50 ml) was stirred at 0° C. for 30 min. Removal of the solvent in vacuo gave a viscous oil which was purified by silica gel column chromatography. Elution with chloroform-methanol (96:4, v/v) yielded 23 (530 mg, 81.5%) as a syrup.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07589077B2
Source datasetuspto-grants-2009_09
ORD IDord-44ab11e8afc34298a45c4f0915e4f448
Source noteuspto-grants-2009_09