4-Fluoroaniline → HCID 86585952, compound
Reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(#N)C>[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (Aldrich, 24 g, 103 mmol) in 250 mL of acetonitrile at room temperature was added 4-fluoroaniline (22.75 g, 205 mmol). After stirring for two days, the mixture was heated at 60° C. for four hours. The resulting solid was filtered and washed with EtOAc. The filtrate was concentrated, diluted in EtOAc (300 L), washed with brine, dried (MgSO4), filtered and concentrated to provide a crude product. The crude product was stirred with hexanes (400 mL) and then filtered to give 23 g of the ethyl 4-(4-fluorophenyl)amino-2-methylthiopyrimidine-5-carboxylate as a white solid.