反応 #73045

反応方程式

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

収率 17.9%

溶媒

DMF

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated under reduced pressure
2. 2
   その他the residue was partitioned between ethyl acetate (700 mL) and saturated aqueous sodium bicarbonate (100 mL)
3. 3
   洗浄The organic layer was washed with water (3×100 mL) and brine (50 mL)
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他to provide an orange solid
8. 8
   その他This material was triturated with ethyl acetate

実験手順

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.

出典