Potassium Hydroxide → 1-(2-Chloro-5-fluoropyrimidin-4-yl)ethanone

Participants

Reaction Steps

A mixture of 2-chloro-4-(1-ethoxyvinyl)-5-fluoropyrimidine (5.23 g, 25.81 mmol) in 3N HCl (100 mL) was stirred at rt for 6 h. Potassium hydroxide (50%) was added to give a cloudy mixture (pH was still less than 1) and extracted cloudy mixture with EtOAc. More potassium hydroxide (50%) was added and extracted with EtOAc. Again, more potassium hydroxide (50%) was added until pH=7 and extracted with EtOAc. The combined organic layer dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 25% EtOAc/Hex) to give the desired product. 1H NMR (400 MHz, CDCl3) δ 8.69 (d, J=2 Hz, 1H), 2.71 (2, 3H); 19F (376 MHz, CDCl3) δ −138.26.

Provenance & Evidence