Water → Methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	Methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate	HCID 57500645	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate	HCID 25252839	84%

Reaction Conditions

Temperature	120 °C

Reaction Steps

Methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate (1.0 eq, 56 mg, 0.175 mmol) was mixed with benzeneboronic acid (2.0 eq, 43 mg, 0.35 mmol), PdCl2(dppf) (0.1 eq, 13 mg, 0.0178 mmol) and cesium carbonate (2.0 eq, 114 mg, 0.35 mmol) in dioxane (0.5 ml). The mixture was stirred for 10 minutes at 120° C. under microwave heating. Water was added and the resulting precipitate was filtered and dried. After trituration in ethylacetate and hexanes, methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate was isolated by filtration (53 mg, 84% yield). LCMS (ES): >90% pure, m/z 362 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07910600B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-7777c8b8edd647be8e5e396c0278ed6d
Source note	uspto-grants-2011_03