(2,6-Dimethoxypyridin-3-yl)boronic acid → N4-Cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine

関与物質

役割	名称	HCID	仕込み量
反応物	(2,6-Dimethoxypyridin-3-yl)boronic acid	HCID 2762707	—
反応物	Dicyclohexyl(2,6-dimethoxyphenyl)phosphine	HCID 57474835	—
反応物	2,2-Dimethyl-3-[2-(5-piperazin-1-yl-pyridin-2-ylamino)-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-9-yl]-propan-1-ol	HCID 58299717	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	1-Butanol	HCID 263	—
生成物	N4-Cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine	HCID 67234124	53%

反応条件

温度	100 °C

反応手順

Compound 2 (2.00 g, 7.78 mmol), 2,6-dimethoxypyridin-3-ylboronic acid (2.13 g, 11.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.214 g, 0.233 mmol), and dicyclohexyl(2,6-dimethoxyphenyl)phosphine (0.156 g, 0.467 mmol), were dissolved in n-butanol (2.5 mL). The reaction was purged with argon and heated at 100° C. for 19 hours. The resulting solution was added to 80 mL water and extracted with ethyl acetate (2×150 mL). The combined organics were dried (MgSO4) and evaporated to give an orange oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-5% methanol) afforded compound 267 as an off-white solid (1.29 g, 53%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08841312B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-d3e19f1ead1e47d29af0c75817adef37
出典メモ	uspto-grants-2014_09