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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 221983Generated: October 26, 2026

1,2-Dichloroethane → 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one

https://huagongshe.com/reaction/221983

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantDiisopropylethylamineHCID 81531—
ReactantPyrimidine-2-carboxylic acidHCID 12626245—
Reactant5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-oneHCID 67076057—
SolventAcetic AcidHCID 176—
SolventDimethylformamideHCID 6228—
Product9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-oneHCID 136352657—

Reaction Conditions

Temperature150 °C

Reaction Steps

To a mixture of 5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one (2-3) (1.4 g, 5.55 mmol), 2-pyrimidinecarboxylic acid (0.69 g, 5.55 mmol), HOBt (0.85 g, 5.55 mmol), and DIPEA (0.97 mL, 5.55 mmol) in DMF (50 mL) was added EDC (1.23 g, 6.66 mmol). After stirring for overnight, AcOH (5 mL) was added, and the mixture was heated under microwave irradiation at 150° C. for 15 minutes. The solvent was removed under reduced pressure, and the residue was diluted with MeOH, and added water. The resulting solid was collected by filtration to give 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one (2-4) as a colorless solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08207169B2
Source datasetuspto-grants-2012_06
ORD IDord-b6e29215f372433f9ed8b85f18948545
Source noteuspto-grants-2012_06