Triethylamine → N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine

참여 물질

역할	이름	HCID	투입량
반응물	Triethylamine	HCID 8471	—
반응물	Trimethylsilylacetylene	HCID 66111	—
반응물	5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine	HCID 68459408	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
용매	Acetonitrile	HCID 6342	—
생성물	N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine	HCID 68459491	—

반응 조건

온도	90 °C

반응 단계

A 75 mL thick wall glass tube with a teflon screw cap was charged with 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine (0.995 g, 3.68 mmol), acetonitrile (9 mL), triethylamine (3.00 ml, 3.68 mmol), dichlorobistriphenylphosphine palladium(II) (0.259 g, 0.368 mmol), copper(I) iodide (0.0351 g, 0.184 mmol), and ethynyltrimethylsilane (0.362 g, 3.68 mmol). The tube was capped and heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine. MS m/z=288 [M+H]+. Calc'd for C14H17N3SSi: 287.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07776869B2
출처 데이터셋	uspto-grants-2010_08
ORD ID	ord-197ab70497624242988968274d900b34
출처 메모	uspto-grants-2010_08