Cesium carbonate → 2,6-dichloro-4-cyano-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-3-nitropyridin-4-yl)benzamide

関与物質

役割	名称	HCID	仕込み量
反応物	Cesium carbonate	HCID 10796	—
反応物	2,6-Dimethyl-4-aminopyrimidine	HCID 68039	—
反応物	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
反応物	N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide	HCID 86648955	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1,2-Dimethoxyethane	HCID 8071	—
溶媒	1,4-Dioxane	HCID 31275	—
生成物	2,6-dichloro-4-cyano-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-3-nitropyridin-4-yl)benzamide	HCID 59618406	5%

反応手順

A 25 mL microwave tube containing N-(2-chloro-3-nitropyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (100 mg, 0.27 mmol), 2,6-dimethylpyrimidin-4-amine (43 mg, 0.35 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), Cs2CO3 (180 mg, 0.54 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 4 mg, 0.005 mmol), dioxane (8 mL) and DME (3 mL) was degassed and then charged by N2 (3×). The mixture was then irradiated in a microwave reactor at 160° C. for 2 hours and then diluted with dioxane (20 mL). The reaction was filtered through Celite and concentrated under reduced pressure. The residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min) to afford the desired product (4 mg, yield: 5%). LCMS (ESI) m/z: 458.3 [M+H+].

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08486950B2
出典データセット	uspto-grants-2013_07
ORD ID	ord-650efcb8aa104dc69f9c83da8e541b8c
出典メモ	uspto-grants-2013_07