Hantzsch ester → 6-Bromo-4-hydroxy-3-(pyrimidin-5-ylmethyl)quinolin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Hantzsch ester	HCID 70849	—
Reactant	Pyrimidine-5-carboxaldehyde	HCID 2761034	—
Reactant	6-Bromo-4-hydroxyquinolin-2(1H)-one	HCID 54689446	—
Reactant	(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol	HCID 118005815	—
Solvent	Ethanol	HCID 702	—
Solvent	Pyridine	HCID 1049	—
Product	6-Bromo-4-hydroxy-3-(pyrimidin-5-ylmethyl)quinolin-2(1H)-one	HCID 118006140	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a dark solution of 6-bromo-4-hydroxyquinolin-2(1H)-one (3.92 g, 16.31 mmol, Intermediate 45: step a) and pyrimidine-5-carbaldehyde (1.94 g, 17.95 mmol) in pyridine (29 mL) was added diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (4.13 g, 16.31 mol). The resulting mixture was warmed with stirring in a 100° C. oil bath for a period of 5 hours. After cooling to room temperature, the mixture was diluted with ethanol. The tan precipitate was isolated by filtration, rinsing further with EtOH then acetonitrile and dried to provide the title compound that was carried to the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09284308B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-a6e1720ab1704de6a75a3c2d387ec0bd
Source note	uspto-grants-2016_03