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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 873549Generated: October 28, 2026

Water → 4-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid amide

https://huagongshe.com/reaction/873549

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
ReactantAzane;hydrateHCID 12896473—
Reactant4-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acidHCID 117700522—
SolventDiethyl EtherHCID 3283—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Product4-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid amideHCID 11770077486%

Reaction Steps

1,1′-Carbonyldiimidazole (50.1 mg, 0.309 mol) was added to a solution of the 4-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid obtained in Example 75-4 (133 mg, 0.257 mmol) in THF (2.0 mL) and DMF (0.5 mL) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 30 minutes. Thereafter, 27% ammonia water was added to the resulting solution, and the mixture thus obtained was further stirred at the same temperature as above for 30 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate twice. The organic layer thus obtained was washed with 1 M-hydrochloric acid and brine, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The residue thus obtained was solidified with diethyl ether to obtain the title compound (114 mg, yield: 86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975263B2
Source datasetuspto-grants-2015_03
ORD IDord-3968d3e88ecd40b0a05d18ea2740eb39
Source noteuspto-grants-2015_03