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

참여 물질

역할	이름	HCID	투입량
반응물	Trimethyl-2-propynylsilane	HCID 83378	—
반응물	2-Amino-3,5-dibromopyrazine	HCID 620004	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
용매	Tetrahydrofuran	HCID 8028	—
용매	Ethyl Acetate	HCID 8857	—
생성물	5-Bromo-3-(3-trimethylsilanyl-prop-1-ynyl)-pyrazin-2-ylamine	HCID 86642304	87.2%

반응 단계

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).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08012974B2
출처 데이터셋	uspto-grants-2011_09
ORD ID	ord-e6cbde8d04c7467f824533ee652c141d
출처 메모	uspto-grants-2011_09