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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 336140Generated: October 29, 2026

Triethylamine → 4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

https://huagongshe.com/reaction/336140

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantMethanesulfonyl chlorideHCID 31297—
ReactantSodium BicarbonateHCID 516892—
Reactant4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-olHCID 86711280—
SolventTetrahydrofuranHCID 8028—
Product4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonateHCID 86711281—

Reaction Steps

Triethylamine (0.157 ml) and methanesulfonyl chloride (0.074 ml) were added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol (288 mg) obtained in Step 8 in THF (5 ml) under ice-cooling. After stirring at the same temperature for 15 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-brown solid (615 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889666B2
Source datasetuspto-grants-2014_11
ORD IDord-e0b5e9bdad224a43b4cb5056569659b7
Source noteuspto-grants-2014_11