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

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	4-Bromo-1,3-benzodioxole	HCID 2776189	—
반응물	2-Chloro-5-methylpyrimidin-4-amine	HCID 4302175	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
용매	Dichloromethane	HCID 6344	—
용매	1,4-Dioxane	HCID 31275	—
생성물	Benzo[1,3]dioxol-4-yl-(2-chloro-5-methyl-pyrimidin-4-yl)-amine	HCID 57674946	39.1%

반응 단계

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)+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07528143B2
출처 데이터셋	uspto-grants-2009_05
ORD ID	ord-75cc7d16f37149ddac111f8ad4152a83
출처 메모	uspto-grants-2009_05