反応 #68652

反応方程式

1-bromo-2-methoxyethane

8-chloro-1,5-naphthyridin-3-amine

DMF

SODIUM HYDRIDE

→

8-chloro-N-(2-methoxyethyl)-1,5-naphthyridin-3-amine

収率 33.1%

溶媒

MeOH Dichloromethane

反応条件

後処理

1. 1
   その他Ice bath removed
2. 2
   その他reaction mixture
3. 3
   温度heated to 85° C.
4. 4
   その他Reaction
5. 5
   洗浄eluted with 2% MeOH/DCM

実験手順

A round bottom flask under nitrogen atmosphere was charged with 8-chloro-1,5-naphthyridin-3-amine (160 mg, 0.89 mmol), DMF (2.2 mL, 0.89 mmol). This was cooled to 0° C. and SODIUM HYDRIDE (60% dispersion in oil) (107 mg, 4.45 mmol) added portionwise. This was quickly followed by addition of 1-bromo-2-methoxyethane (0.12 mL, 1.25 mmol) dropwise via syringe. Ice bath removed and reaction mixture heated to 85° C. and stirred at this temperature for 16 hours. Reaction diluted with 5 mL of 5% MeOH/Dichloromethane, loaded onto silica gel column and eluted with 2% MeOH/DCM to afford 8-chloro-N-(2-methoxyethyl)-1,5-naphthyridin-3-amine (70 mg, 33% yield) as a light yellow solid.

出典