Cesium carbonate → 9-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-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	5-(3-Bromo-2-fluoropyridin-4-yl)-N4-(cyclopropylmethyl)pyrimidine-2,4-diamine	HCID 58299557	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
生成物	9-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine	HCID 58300071	79%

反応条件

温度	100 °C

反応手順

To a vacuum to argon purged vial containing 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.017 g, 0.030 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.014 g, 0.015 mmol), cesium carbonate (0.19 g, 0.59 mmol) and compound 240 (0.100 g, 0.30 mmol) was added degassed dioxane (2.00 mL). The reaction was stirred at 100° C. After 4 h, the reaction was cooled and applied directly to silica. Silica gel chromatography (gradient elution 40 to 90% ethyl acetate in hexanes) afforded compound 241 (0.060 g, 79% yield). 1H NMR (500 MHz, CDCl3) δ ppm 0.45-0.57 (m, 4 H) 1.34-1.47 (m, 1 H) 4.32 (d, J=7.09 Hz, 2 H) 5.46 (br. s., 2 H) 7.68 (dd, J=5.26, 2.81 Hz, 1 H) 8.02 (dd, J=5.13, 1.71 Hz, 1 H) 8.93 (s, 1 H).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08980903B2
出典データセット	uspto-grants-2015_03
ORD ID	ord-29f3bc1f545f435782629b536169336e
出典メモ	uspto-grants-2015_03