Реакция #73045

Уравнение реакции

2,4-dichloro-5,6-dimethyl-3-nitropyridine

4-(aminomethyl)tetrahydro-2H-pyran-4-ol

Triethylamine

→

4-{[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

Выход 17.9%

Растворители

DMF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
2. 2
   Другоеthe residue was partitioned between ethyl acetate (700 mL) and saturated aqueous sodium bicarbonate (100 mL)
3. 3
   ПромывкаThe organic layer was washed with water (3×100 mL) and brine (50 mL)
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   Другоеto provide an orange solid
8. 8
   ДругоеThis material was triturated with ethyl acetate

Методика

Under a nitrogen atmosphere 2,4-dichloro-5,6-dimethyl-3-nitropyridine (25 g, 113 mmol) was added to a solution of 4-(aminomethyl)tetrahydro-2H-pyran-4-ol (17 g, 130 mmol) in DMF (375 mL). Triethylamine (18 mL, 130 mmol) was added slowly and the reaction mixture was stirred at ambient temperature over the weekend. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (700 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic layer was washed with water (3×100 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide an orange solid. This material was triturated with ethyl acetate to provide 6.38 g of 4-{[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol as a yellow solid. An additional 4.36 g of product was recovered from the mother liquor.

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