Cesium carbonate → N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2,6-Dimethyl-4-aminopyrimidine	HCID 68039	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-chloro-5-nitropyridin-4-amine	HCID 10910058	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine	HCID 67128909	23.2%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a 200 ml flask was added 4-amino-2-chloro-5-nitropyridine (1.00 g, 5.76 mmol), 4-amino-2,6-dimethylpyrimidine (1.42 g, 11.5 mmol), Pd2(dba)3 (0.528 g, 0.576 mmol), XantPhos (0.400 g, 0.691 mmol), Cs2CO3 (4.13 g, 12.7 mmol) and dioxane (45 mL). The mixture was degassed with N2 for 2 min and then heated at 110° C. for 16 hrs. After cooling to room temperature the reaction was filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane) to give N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, yield: 23%). LCMS (ESI) m/z: 261.2 [M+H+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08486950B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-761d0ebbebfe4858934c252f17f95520
Source note	uspto-grants-2013_07