5-(Trifluoromethyl)pyrazin-2-amine → [2-(2,6-Dichloro-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(5-trifluoromethyl-pyrazin-2-yl)-amine

https://huagongshe.com/ko/reaction/60203

참여 물질

역할	이름	HCID	투입량
반응물	5-(Trifluoromethyl)pyrazin-2-amine	HCID 13341115	—
반응물	Sodium t-butoxide	HCID 23676156	—
반응물	7-Chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine	HCID 57742463	—
촉매	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
촉매	Ditert-butyl(cyclopenta-1,3-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 12024214	—
용매	Toluene	HCID 1140	—
생성물	[2-(2,6-Dichloro-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(5-trifluoromethyl-pyrazin-2-yl)-amine	HCID 42642035	—

반응 조건

온도	90 °C

반응 단계

To a mixture of 7-chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine (113 mg, 0.34 mmol), 1,2,3,4,5-pentaphenyl-1-(di-t-butylphosphino)ferrocene (49 mg, 0.07 mmol), tris(dibenzylideneacetone)dipalladium (0) (31 mg, 0.03 mmol), and 5-trifluoromethyl-pyrazin-2-ylamine (66 mg, 0.41 mmol) in toluene (3 mL) was added NaOtBu (40 mg, 0.41 mmol) at rt. The mixture was heated to 90° C. under N2. After 18 h, the reaction mixture was cooled and filtered through a pad of diatomaceous earth, eluting with MeOH (30 mL). The filtrate was concentrated and the crude residue was purified using preparative reverse-phase HPLC to afford the title compound a colorless solid (43 mg, 28%). MS (ESI): mass calcd. for C17H9Cl2F3N6S, 455.9; m/z found, 457.0 [M+H]+. 1H NMR ((CD3)250): 10.77 (s, 1H), 9.49 (s, 1H), 8.88-8.87 (m, 1H), 8.75 (s, 1H), 7.59 (d, J=8.0 Hz, 2H), 7.45 (dd, J=8.5, 7.7 Hz, 1H), 4.83 (s, 2H).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09440978B2
출처 데이터셋	uspto-grants-2016_09
ORD ID	ord-60d87fc246db407c813b239fae238976
출처 메모	uspto-grants-2016_09