(Bis(2-methoxyethyl)amino)sulfur trifluoride → 2-Chloro-4-(1-fluoroethyl)pyrimidine
Reaction equation
COCCN(S(F)(F)[F:11])CCOC.[Cl:14][C:15]1[N:20]=[C:19]([CH:21](O)[CH3:22])[CH:18]=[CH:17][N:16]=1>ClCCl>[Cl:14][C:15]1[N:20]=[C:19]([CH:21]([F:11])[CH3:22])[CH:18]=[CH:17][N:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Bis(2-methoxyethyl)aminosulfur trifluoride (7.70 g, 17.4 mmol) was added drop wise to a solution of 1-(2-chloropyrimidin-4-yl)ethanol (2.30 g, 14.5 mmol) in dichloromethane (20 mL) at 0° C. and the mixture was stirred at 0° C. for 15 minutes. The mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate. The organic layers were separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 2-chloro-4-(1-fluoroethyl)pyrimidine. 1H NMR (500 MHz, DMSO-d6) δ 8.66 (d, J=5.0 Hz, 1H), 7.45 (d, J=5.0 Hz, 1H), 5.65-5.51 (m, 1H), 1.71-1.65 (m, 3H).