Cesium carbonate → (4-Chloro-3-methyl-phenyl)-(2-chloro-5-methyl-pyrimidin-4-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	5-Bromo-2-chlorotoluene	HCID 609899	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-Chloro-5-methylpyrimidin-4-amine	HCID 4302175	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(4-Chloro-3-methyl-phenyl)-(2-chloro-5-methyl-pyrimidin-4-yl)-amine	HCID 57516501	38.2%

Reaction Steps

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.34 g, 2.34 mmol), 4-bromo-1-chloro-2-methyl-benzene (0.58 g, 2.8mmol), Pd2(dba)3 (0.21 g, 0.23 mmol), Xantphos (0.47 g, 0.47 mmol) and cesium carbonate (2.3 g, 7 mmol) were suspended in dioxane (9 mL) microwaved at 160° C. for 20 min. The reaction mixture was cooled to room temperature and centrifuged down. Solvents were then decanted and evaporated. Resulting residue was purified by Hash chromatography on silica gel to afford title compound as yellow solids (0.24 g, 38%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08133900B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-173a5f732f8c4b3c9742af166aec9d53
Source note	uspto-grants-2012_03