Triethylamine → [2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine

참여 물질

역할	이름	HCID	투입량
반응물	Triethylamine	HCID 8471	—
반응물	3,3-Diethoxypropyne	HCID 66285	—
반응물	5-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amine	HCID 58015891	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
촉매	HCID 178418476	HCID 178418476	—
용매	Dimethylformamide	HCID 6228	—
생성물	[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine	HCID 58015829	37.2%

반응 조건

온도	55 °C

반응 단계

To a mixture of (5-Bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (420 mg, 1.5 mmol) and propiolaldehyde diethyl acetal (0.32 mL, 2.25 mmol) in DMF (6 mL) is added PdCl2(PPh3)2 (105 mg, 0.15 mmol) and CuI (28 mg, 0.15 mmol), followed by Et3N (0.42 mL, 3 mmol). The mixture is degassed and heated at 55° C. for 16 h. Then the mixture is cooled down to room temperature, diluted with EtOAc, washed with water and brine. The organic layer is dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, EtOAc:Heptane=5:95 to 40:60) to give 182 mg of the title compound as a light brown oil.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08324225B2
출처 데이터셋	uspto-grants-2012_12
ORD ID	ord-fa114cb528b84c98bb42002586611d0e
출처 메모	uspto-grants-2012_12