Cesium carbonate → 2-(2-Methoxy-ethylamino)-5-(pyrimidin-5-ylamino)-pyrimidine-4-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Pyrimidin-5-amine	HCID 344373	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethyl 5-bromo-2-((2-methoxyethyl)amino)pyrimidine-4-carboxylate	HCID 58368043	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(2-Methoxy-ethylamino)-5-(pyrimidin-5-ylamino)-pyrimidine-4-carboxylic acid ethyl ester	HCID 70097510	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

A microwave reaction tube was charged with a suspension of 5-bromo-2-(2-methoxy-ethylamino)-pyrimidine-4-carboxylic acid ethyl ester (30 mg, 0.1 mmol), 5-aminopyrimidine (14 mg, 0.15 mmol) and cesium carbonate (45 mg, 0.14 mmol) in dioxane (0.6 ml) and flushed with argon. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 19 mg, 32 μmol) and tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (10 mg, 10 μmol) were consecutively added and the reaction tube was sealed and stirred overnight at 130° C. After cooling-down to ambient temperature, the reaction mixture was filtrated. The filtrate was concentrated in vacuo and the product was obtained after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (11 mg, 35%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623866B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-feb0c6db266049e3946c75d395e35412
Source note	uspto-grants-2014_01