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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 480108Generated: October 30, 2026

Methanol → 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

https://huagongshe.com/reaction/480108

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantSodium BicarbonateHCID 516892—
Reactant4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acidHCID 9886589—
CatalystSulfuric AcidHCID 1118—
SolventEthyl AcetateHCID 8857—
Product4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl esterHCID 984406097%

Reaction Steps

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (Example 13) (1.50 g, 3.86 mmol) was combined with 60 ml of MeOH, and 10 drops of conc'd H2SO4. The reaction solution was brought to reflux until consumption of starting material ceased. Sat'd NaHCO3 was then added until neutral pH and the reaction mixture was conc'd in vacuo. The residue was taken up in EtOAc and washed with sat'd NaHCO3, brine, and dried over Na2SO4. The EtOAc solution was conc'd in vacuo to give 1.51 g (97% yield) of a white solid. (MH+=403.13)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06649600B1
Source datasetuspto-grants-2003_11
ORD IDord-86dbde1489974cb09f8bfc93938ff989
Source noteuspto-grants-2003_11