Trimethyl-2-propynylsilane → 5-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine

関与物質

役割	名称	HCID	仕込み量
反応物	Trimethyl-2-propynylsilane	HCID 83378	—
反応物	2-Amino-3,5-dibromopyrazine	HCID 620004	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Tetrahydrofuran	HCID 8028	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	5-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine	HCID 86642304	87.2%

反応手順

3,5-Dibromo-pyrazin-2-ylamine (1.70 g, 6.70 mmol), TEA (1.1 mL, 8.04 mmol), PdCl2(PPh3)4 (28 mg, 0.040 mmol), and CuI (15 mg, 0.080 mmol) were dissolved in THF (17 mL), cooled to RT and Trimethyl-prop-2-ynyl-silane (1.0 mL, 6.7 mmol) was added at 0° C., allowed to warm up to RT and stirred overnight. The reaction mixture was diluted with EtOAc, washed with H2O and saturated aqueous NaHCO3, dried (MgSO4) and concentrated, and purified by SiO2 chromatography (80 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 1.66 g of 5-bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine as a yellow semi-solid contaminated by starting material (87% yield, 66% purity).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08012974B2
出典データセット	uspto-grants-2011_09
ORD ID	ord-e6cbde8d04c7467f824533ee652c141d
出典メモ	uspto-grants-2011_09