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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 454269Generated: October 26, 2026

Potassium Carbonate → 7-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}-6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazoline

https://huagongshe.com/reaction/454269

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant1-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineHCID 10642851—
Reactant7-Hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazolineHCID 135763115—
SolventDimethylformamideHCID 6228—
Product7-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}-6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazolineHCID 2203059963%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (1.00 g, 3.11 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (1.288 g, 9.33 mmol) and 4-(4-methylphenylsulphonyloxymethyl)-1-tert-butoxycarbonylpiperidine (1.264 g, 3.42 mmol), (prepared as described for the starting material in Example 10), in DMF (35 ml) was stirred at 80° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography, 5% methanol/95% dichloromethane and the product was recrystallised from ethanol to give 6-methoxy-4-(3-methylindol-5-yloxy)-7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)quinazoline (1.011 g, 63%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08492560B2
Source datasetuspto-grants-2013_07
ORD IDord-5de24ecf6ea44bb2b15277dd367e4206
Source noteuspto-grants-2013_07