Cesium carbonate → Benzo[1,3]dioxol-4-yl-(2-chloro-5-methyl-pyrimidin-4-yl)-amine

関与物質

役割	名称	HCID	仕込み量
反応物	Cesium carbonate	HCID 10796	—
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	4-Bromo-1,3-benzodioxole	HCID 2776189	—
反応物	2-Chloro-5-methylpyrimidin-4-amine	HCID 4302175	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	Dichloromethane	HCID 6344	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	Benzo[1,3]dioxol-4-yl-(2-chloro-5-methyl-pyrimidin-4-yl)-amine	HCID 57674946	39.1%

反応手順

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (1.4 g, 9.7 mmol), 4-bromo-benzo[1,3]dioxole (2.0 g, 10 mmol), Pd2(dba)3 (0.80 g, 0.87 mmol), Xantphos (1.0 g, 1.7 mmol) and cesium carbonate (6.3 g, 19 mmol) was suspended in dioxane (40 mL) and heated at reflux under the argon atmosphere for 5 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 purified by flash chromatography on silica gel (hexanes to 50% EtOAc/hexanes) to afford the title compound (1.0 g, 39%) as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 2.13 (s, 3H), 5.99 (s, 2H), 6.80-6.90 (m, 3H), 8.01 (s, 1H), 8.92 (s, 1H). MS (ES+): m/z 264 (M+H)+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07528143B2
出典データセット	uspto-grants-2009_05
ORD ID	ord-75cc7d16f37149ddac111f8ad4152a83
出典メモ	uspto-grants-2009_05