Реакция #1899004

Уравнение реакции

1,4-Dioxane

5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid

2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine

Na2CO3

→

2-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine

Выход 48.3%

Растворители

water

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   Фильтрацияthe mixture was filtered
3. 3
   Промывкаwashed with EtOAc (2×20 mL)
4. 4
   Концентрированиеthe combined organic phases were concentrated
5. 5
   Другоеchromatographed through a Redi-Sep pre-packed silica gel column (hexanes to 30% ethyl acetate in hexanes)

Методика

1,4-Dioxane (16 mL) and water (3.3 mL) were added to a mixture of 5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid (0.715 g, 3.53 mmol), 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (0.682 g, 3.88 mmol), Pd(PPh3)4 (0.408 g, 0.353 mmol), and Na2CO3 (0.935 g, 8.82 mmol) and the suspension was heated at 90° C. for 2 h. After cooling, the mixture was filtered, washed with EtOAc (2×20 mL), and the combined organic phases were concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (hexanes to 30% ethyl acetate in hexanes) to give 2-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine (0.5259 g, 1.706 mmol, 48.3% yield) as a white solid. LCMS (API-ES) m/z 309 (M+H)+.

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