反応 #40928

反応方程式

1-bromo-3-chloropropane

I2

NaOH

5-fluoro-2,4-bis[(trimethylsilyl)oxy]pyrimidine

→

title compound

1-(3-chloropropyl)-5-fluoro-2,4(1H,3H)-pyrimidinedione

溶媒

1,2-dichloroethane

water

反応条件

後処理

1. 1
   温度to reflux for 30 h
2. 2
   抽出the mixture was extracted twice with DCM
3. 3
   乾燥the organic phase dried over Na2SO4
4. 4
   その他the solvent evaporated under reduced pressure
5. 5
   その他The crude product was purified by flash chromatography on silica gel eluting with DCM/MeOH 95/5

実験手順

A mixture of 5-fluoro-2,4-bis[(trimethylsilyl)oxy]pyrimidine (1 g, commercially available from Lancaster), 1-bromo-3-chloropropane (0.44 mL) and I2 (10 mg) in 1,2-dichloroethane (10 mL) was heated to reflux for 30 h. Then the reaction mixture was treated with water and the pH was brought to 7 using aqueous 6N NaOH solution, the mixture was extracted twice with DCM, the organic phase dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with DCM/MeOH 95/5 to give 35 mg of the title compound.

出典