Sodium Carbonate → 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine	HCID 2795361	—
Reactant	7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one	HCID 86667983	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one	HCID 68107879	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

To a solution of 7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (750 mg, 2.26 mmol) in 1,4-dioxane (11 mL) were added 4-morpholinophenylboronic acid pinacol ester (654 mg, 2.26 mmol), 2M aqueous Na2CO3 solution (3.39 mL, 6.78 mmol), and Pd(dppf)2Cl2 (36.9 mg, 0.045 mmol). The reaction mixture was purged with N2 and heated at 140° C. by a microwave reactor for 15 minutes. The mixture was then cooled, quenched with H2O (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layer was dried over MgSO4 and evaporated under reduced pressure to afford crude 5-(4-methoxybenzyloxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08722692B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-a86b379a273b41e59f6b27681b101ee3
Source note	uspto-grants-2014_05