Acetic Acid → 7-Chloro-3-(3,5-dimethylphenyl)-4-hydroxy-2-oxo-1,2-dihydroquinoline-6-carboxylic acid pyrimidin-4-ylamide

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Dimethyl Sulfoxide	HCID 679	—
Reactant	4-Aminopyrimidine	HCID 68958	—
Reactant	7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodoquinolin-2(1H)-one	HCID 54711239	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	7-Chloro-3-(3,5-dimethylphenyl)-4-hydroxy-2-oxo-1,2-dihydroquinoline-6-carboxylic acid pyrimidin-4-ylamide	HCID 54730097	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To 20 mL dry methylsulfoxide was added sequentially 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodo-1H-quinolin-2-one (EXAMPLE 4.2 Step B, 1.0 g), 4-dimethylaminopyridine (860 mg), 4-aminopyrimidine (90 mg), [1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) and the mixture heated to 100° C. under an atmosphere of carbon monoxide. After 72 hours, the mixture was cooled to room temperature and poured into 200 mL ice/water. The pH of the resulting solution was adjusted to pH4 by the addition of acetic acid. The resulting solids were collected by filtration and then re-purified by flash chromatography on silica gel (chlorofonm:methanol, 95:5) to give the title compound (400 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06150352
Source dataset	uspto-grants-2000_11
ORD ID	ord-dfc0be174c404b838de58a80a4e9758b
Source note	uspto-grants-2000_11