Cesium carbonate → [2-(5-Chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-(3-fluoro-pyridin-4-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Chlorimide	HCID 76939	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	4-Amino-3-fluoropyridine	HCID 817122	—
Reactant	4-Chloro-2-(5-chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidine	HCID 21113093	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[2-(5-Chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-(3-fluoro-pyridin-4-yl)-amine	HCID 21113088	21.7%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a suspension of dioxane (5 ml), Pd(OAc)2 (50 mg), BINAP (20 mg), 4-amino-3-fluoro-pyridine (42 mg) and Cs2CO3 (200 mg) was added the crude imino chloride, 4-Chloro-2-(5-Chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidine (100 mg, 0.34 mmol) in a sealed tube. The reaction mixture was heated to 110° C. for 15 h. The reaction mixture was cooled to r.t. and filtered through Celite® and the crude material was purified by silica gel flash column chromatography (95% to 5% gradient CH2Cl2/EtOAc) to afford [2-(5-Chloro-2 -fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-(3-fluoro-pyridin-4-yl)-amine (27.3 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07232824B2
Source dataset	uspto-grants-2007_06
ORD ID	ord-f160a7ac685243b48eb237fa92fb6276
Source note	uspto-grants-2007_06