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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1912177Generated: November 3, 2026

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

https://huagongshe.com/reaction/1912177

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Reactant2-Chloro-5-methylpyrimidin-4-amineHCID 4302175—
Reactant3-Bromo-N-tert-butylbenzene-1-sulfonamideHCID 4820926—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventDichloromethaneHCID 6344—
Solvent1,4-DioxaneHCID 31275—
ProductN-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamideHCID 53401091120.8%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08604042B2
Source datasetuspto-grants-2013_12
ORD IDord-d97b34cdbf204d21935cfb982f4dae1f
Source noteuspto-grants-2013_12