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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1754255Generated: November 1, 2026

Hydrochloric Acid → 5-(Benzyloxy)-2-methoxy-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

https://huagongshe.com/reaction/1754255

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
Reactanttert-Butyl 5-(benzyloxy)-2-methoxy-6-oxo-1,6-dihydropyrimidine-4-carboxylateHCID 136338080—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product5-(Benzyloxy)-2-methoxy-6-oxo-1,6-dihydropyrimidine-4-carboxylic acidHCID 13633808189.4%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of Compound 46d (1.1 g, 3.2 mmol) in MeOH (20 mL) and THF (20 mL) was added 7 N NaOH (4.0 mL, 28 mmol) and the solution stirred at 50° C. for 3 h. The reaction mixture was cooled in an ice bath then acidified by the addition of 1 N HCl (20 mL). The resulting precipitate was filtered, rinsed with water then dried under vacuum to give Compound 46a (790 mg, 89% yield) as a white solid. LCMS ESI 277.0 (M+H), RT=1.41 min (Method Q). 1H NMR (400 MHz, DMSO-d6) δ 13.49 (br. s., 1H), 12.91 (br. s., 1H), 7.90-6.67 (m, 5H), 5.01 (s, 2H), 3.86 (s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09169240B2
Source datasetuspto-grants-2015_10
ORD IDord-811d51ab1187460b92506a0ec40a6928
Source noteuspto-grants-2015_10