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

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Cesium carbonate	HCID 10796	—
Edukt	4-Bromo-2-chloro-alpha,alpha,alpha-trifluorotoluene	HCID 67959	—
Edukt	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Edukt	2-Chloro-5-methylpyrimidin-4-amine	HCID 4302175	—
Katalysator	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Lösungsmittel	1,4-dioxane N,N-dimethylformamide	HCID 21712069	—
Produkt	(2-Chloro-5-methyl-pyrimidin-4-yl)-(4-chloro-3-trifluoromethyl-phenyl)-amine	HCID 57516506	96,1%

Reaktionsschritte

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.30 g, 2.1 mmol), 4-bromo-1-chloro-2-trifluoromethyl-benzene (0.40 mL, 2.7 mmol), Pd2(dba)3 (0.10 g, 0.11 mmol), Xantphos (0.13 g, 0.22 mmol) and cesium carbonate (1.5 g, 4.6 mmol) in dioxane/DMF (6/1, 7 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160° C. for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (hexanes to 50% EtOAc/hexanes) to afford the title compound (0.65 g, 96%) as a white solid. MS (ES+): m/z 322 (M+H)+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07528143B2
Quelldatensatz	uspto-grants-2009_05
ORD ID	ord-7bea1b9d67a64ad8a613a48b0c7e6663
Quellennotiz	uspto-grants-2009_05