Cesium carbonate → 2-Chloro-5-methyl-N-(2,3-dimethylphenyl)pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-Bromo-o-xylene	HCID 68472	—
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	2-Chloro-5-methyl-N-(2,3-dimethylphenyl)pyrimidin-4-amine	HCID 57516494	—

Reaction Steps

A mixture of 2-chloro-5-methylpyrimidin-4-amine (143.6 mg, 1 mmol), 1-bromo-2,3-dimethylbenzene (222 mg, 1.2 mmol), Pd2(dba)3 (92 mg, 0.1 mmol), Xantphos (174 mg, 0.3 mmol) and cesium carbonate (1.3 g, 4 mmol) were suspended in dioxane (150 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (10 mL) and added hexanes (100 mL). The solid was collected by filtration and washed with hexanes to afford the crude title compound as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08133900B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-95e1ea27c6ca46138a74577cde58013f
Source note	uspto-grants-2012_03