Potassium Phosphate, Tribasic → HCID 70097755, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Pyrimidin-5-amine	HCID 344373	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Methyl 5-bromo-2-methylpyrimidine-4-carboxylate	HCID 44631874	—
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	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Ethylacetate heptane	HCID 21899848	—
Product	HCID 70097755	HCID 70097755	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A suspension of 5-bromo-2-methylpyrimidine-4-carboxylic acid methyl ester (89.1 mg, 386 μmol), 5-aminopyrimidine (55.0 mg, 578 μmo) and potassium phosphate tribasic (115 mg, 540 μmol) in toluene (3 mL) was evacuated and flushed with argon. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 73.6 mg, 127 μmol) and tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (39.9 mg, 38.6 μmol) were added and the reaction mixture was stirred at 120° C. for 16 h. The reaction mixture was poured into ethyl acetate (50 mL) and extracted with water. The organic phase was washed brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and the solvent was removed. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (55 mg, 58%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623866B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-e54b3c4dd6f14165842f19500fc404c5
Source note	uspto-grants-2014_01