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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206278Generated: November 4, 2026

Malononitrile → 7-Amino-5-(3-bromo-4,5-dimethoxy-phenyl)-2,4-dimethyl-5H-pyrano[2,3-d]pyrimidine-6-carbonitrile

https://huagongshe.com/reaction/2206278

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMalononitrileHCID 8010—
ReactantDabcoHCID 9237—
Reactant3-Bromo-4,5-dimethoxybenzaldehydeHCID 81379—
ReactantHCID 178429343HCID 178429343—
SolventEthanolHCID 702—
SolventWaterHCID 962—
Product7-Amino-5-(3-bromo-4,5-dimethoxy-phenyl)-2,4-dimethyl-5H-pyrano[2,3-d]pyrimidine-6-carbonitrileHCID 69636740—

Reaction Conditions

Temperature80 °C

Reaction Steps

4-Hydroxy-2,6-dimethylpyrimidine (546 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol) and then stirred at 80° C. under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50% aqueous ethanol and dried under vacuum (1.52 g, 3.64 mmol, 82.8%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09371333B2
Source datasetuspto-grants-2016_06
ORD IDord-a6c82628e2814ca98f2391cee6495021
Source noteuspto-grants-2016_06