Cesium carbonate → N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	2-Methoxypyrimidin-5-amine	HCID 352904	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	2-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 71575645	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
용매	1,4-Dioxane	HCID 31275	—
생성물	N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide	HCID 90040888	60%

반응 조건

온도	150 °C

반응 단계

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 μmol), 2-methoxypyrimidin-5-amine (65.9 mg, 526 μmol), xantphos (60.9 mg, 105 μmol), Pd2(dba)3 (32.1 mg, 35.1 μmol) and cesium carbonate (229 mg, 702 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 40-80% ethyl acetate in hexanes) to give N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (99 mg, 210 μmol, 60%) as a yellow solid. (EI/CI) m/z: 484.3 [M+H].

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09334278B2
출처 데이터셋	uspto-grants-2016_05
ORD ID	ord-d228af7516b042769206e5970c214555
출처 메모	uspto-grants-2016_05