Binap, (A+-)- → [4-(2-Morpholin-4-yl-pyrimidin-4-ylamino)-naphthalen-1-yl]-oxo-acetic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	2-(Morpholin-4-yl)pyrimidin-4-amine	HCID 20228619	—
Reactant	(4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester	HCID 59379801	—
Solvent	Toluene	HCID 1140	—
Solvent	palladium(II) acetate	HCID 167845	—
Product	[4-(2-Morpholin-4-yl-pyrimidin-4-ylamino)-naphthalen-1-yl]-oxo-acetic acid methyl ester	HCID 59379827	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

2-Morpholin-4-yl-pyrimidin-4-ylamine (140 mg, 0.77 mmol) and (4-bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester (18) (228 mg, 0.77 mmol) were suspended in 5 mL toluene and Pd(OAc)2 (5 mg, 3 mol %), BINAP (24 mg, 5 mol5) and CS2CO3 (753 mg, 2031 mmol) were added. The reaction mixture was stirred at 100° C. for 24hrs. The cooled mixture was purified by column chromatography (0-100% EtOAc/Hex) to yield 169 mg of target product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07749999B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-20e408c885394977afa5870433a9b291
Source note	uspto-grants-2010_07