2-Nitroaniline → N-(2-Nitro-phenyl)-N'-pyridin-4-ylmethyl-pyrimidine-4,6-diamine

Participants

Role	Name	HCID	Charge
Reactant	2-Nitroaniline	HCID 6946	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Chloro-N-(4-pyridinylmethyl)-4-pyrimidinamine	HCID 46741435	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	N-(2-Nitro-phenyl)-N'-pyridin-4-ylmethyl-pyrimidine-4,6-diamine	HCID 118026209	45.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A degassed mixture of (6-chloro-pyrimidin-4-yl)-pyridin-4-ylmethyl-amine (500 g, 2.27 mmol), 2-nitroaniline (317 g, 2.3 mmol), Pd2(dba)3 (200 g, 0.22 mmol), Xantphos (253 g, 0.44 mmol) and Cs2CO3 (1.48 g, 9.35 mmol) in toluene (10 mL) was heated at 100° C. for 3 hours. The reaction was concentrated, and the residue was purified by reverse phase chromatography followed by flash chromatography on silica to obtain the title compound (330 mg, yield: 45%). MS (ESI): 323 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434697B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-6256a2396df5471b87ce602159f413ad
Source note	uspto-grants-2016_09