Реакция #1899005

Уравнение реакции

LiHMDS

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

5-amino-2-methoxypyridine

THF

→

5-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amine

Выход 6.2%

Растворители

ethyl acetate

NH4Cl

water

Условия реакции

Обработка

1. 1
   ЭкстракцияThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
2. 2
   Промывкаthe combined organic layers were washed with brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеthe residue was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., hexanes to 50% ethyl acetates in hexanes)

Методика

LiHMDS (1.0 M in THF, 4.14 mL, 4.14 mmol) was added to a stirred solution of 2-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine (0.425 g, 1.379 mmol) and 5-amino-2-methoxypyridine (0.257 g, 2.068 mmol) in THF (3.00 mL, 36.6 mmol) at 0° C. and the mixture was stirred at the same temperature for 1 h. The reaction mixture was diluted with NH4Cl (aq) and water (10 mL each) and diluted with ethyl acetate (10 mL). The separated aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, concentrated and the residue was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., hexanes to 50% ethyl acetates in hexanes) to give 5-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amine (35 mg, 0.085 mmol, 6.15% yield) as a yellow solid. LCMS (API-ES) m/z 413 (M+H)+.

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