Cesium carbonate → N-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
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	—
Reactant	3-Bromo-N-tert-butylbenzene-1-sulfonamide	HCID 4820926	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamide	HCID 53401091	120.8%

Reaction Steps

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.4 g, 2.8 mmol), 3-bromo-N-tert-butyl-benzenesulfonamide (1.0 g, 3.4 mmol), Pd2(dba)3 (0.17 g, 0.19 mmol), Xantphos (0.2 g, 3.5 mmol) and cesium carbonate (2.0 g, 6.1 mmol) was suspended in dioxane (25 mL) and heated at reflux under the argon atmosphere for 3 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and hexanes added until solid precipitated. After filtration, the title compound (1.2 g, 98%) was obtained as a light brown solid. It was used in the next step without purification. MS (ES+): m/z 355 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07528143B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-e93a811e586543f69f028f13e28bf4a4
Source note	uspto-grants-2009_05