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HRID 491229作成日:2026年10月26日

Cesium carbonate → 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine

https://huagongshe.com/reaction/491229

反応式

関与物質

役割名称HCID仕込み量
反応物Cesium carbonateHCID 10796—
反応物3-BromopyridineHCID 12286—
反応物2-Chloro-5-methylpyrimidin-4-amineHCID 4302175—
触媒1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
触媒Bis(dibenzylideneacetone)palladiumHCID 9811564—
溶媒1,4-DioxaneHCID 31275—
生成物2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amineHCID 5751650557.1%

反応手順

A mixture of 3-bromopyridine (379 mg, 2.4 mmol), 4-amino-2-chloro-5-methylpyrimidine (287 mg, 2.0 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), xantphos (23 mg, 0.04 mmol) and cesium carbonate (975 mg, 3.0 mmol) in dioxane (15 mL) was heated under refluxed for 1 h under argon. The solvent was removed and the residue on purification by HPLC gave an intermediate, 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine as yellow solid (252 mg, 57%). For second Buckwald, a mixture of 2-chloro-5-methyl-N-(pyridin-3-yl)pyrimidin-4-amine (80 mg, 0.36 mmol), 4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine (74 mg, 0.34 mmol), Pd2(dba)3 (3.2 mg, 0.003 mmol), xantphos (4.2 mg, 0.007 mmol) and cesium carbonate (234 mg, 0.72 mmol) in dioxane (5 mL) was heated under refluxed for 1 h under argon. The crude reaction mixture on purification using HPLC gave the title compound as light brown solid (28 mg, 20%).

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US07528143B2
出典データセットuspto-grants-2009_05
ORD IDord-791f3c64b07a45f48d9b42c795804a38
出典メモuspto-grants-2009_05