Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 336141Generated: October 29, 2026

Water → 8-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

https://huagongshe.com/reaction/336141

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium AzideHCID 33557—
Reactant4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonateHCID 86711281—
SolventDimethylformamideHCID 6228—
Product8-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amineHCID 8671128277%

Reaction Conditions

Temperature80 °C

Reaction Steps

Sodium azide (361 mg) was added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate (758 mg) obtained in Step 9 in DMF (9 ml) at room temperature, and the mixture was stirred at 80° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a yellow solid (508 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889666B2
Source datasetuspto-grants-2014_11
ORD IDord-21f0adb07a4a460ea9c3f56ae98b71de
Source noteuspto-grants-2014_11