Phosphorus tribromide → [(2-Chlorophenyl)amino]-n-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([CH2:18]O)=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1)=[O:10].P(Br)(Br)[Br:23]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([CH2:18][Br:23])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1)=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
[(2—Chlorophenyl)amino]-N-[5-(hydroxymethyl)-2-methylthiopyrimidin-4-yl]carboxamide (1363 g) was mixed with 8L of tetrahydrofuran and mechanical stirring begun under nitrogen. Then phosphorus tribromide (135 mL) in 800 mL tetrahydrofuran were added to the mixture over 15 minutes. Stirring was continued for 4 hours, at which time the reaction was stopped and filtered. The filter cake was washed once with tetrahydrofuran and dried overnight at 55° C. in vacuum oven to give 1360 g (71%) of [(2-chlorophenyl)amino]-N-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamide (M+1 377).