Water → 2-Pyridinecarboxylic acid, 6-chloro-3-(5-pyrimidinylamino)-, ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Bromopyrimidine	HCID 78344	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethyl 3-amino-6-chloropyridine-2-carboxylate	HCID 53404472	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	O-Xylene	HCID 7237	—
Product	2-Pyridinecarboxylic acid, 6-chloro-3-(5-pyrimidinylamino)-, ethyl ester	HCID 86660193	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

A suspension of 3-amino-6-chloro-pyridine-2-carboxylic acid ethyl ester (200 mg, 1.0 mmol), 5-bromopyrimidine (444 mg, 2.8 mmol), potassium carbonate (496 mg, 3.6 mmol) and water (76 μl, 4.4 mmol) in o-xylene was evacuated and vented with argon. Palladium(II) acetate (27 mg, 0.12 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos; 87 mg, 0.15 mmol) were added under argon and the reaction mixture was stirred at 140° C. for 60 h. After cooling down to ambient temperature, the reaction mixture was diluted with dichloromethane and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (98 mg, 35%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623866B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-b5d1ba35b4244dc18469ff0f31a1befd
Source note	uspto-grants-2014_01