2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidine → 2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine
Reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[CH2:3][Mg]Br.[CH3:8][S:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]2[C:22]([F:23])=[CH:21][C:20]([F:24])=[CH:19][C:18]=2[F:25])=[C:12](Cl)[N:11]=1>C1(C)C=CC=CC=1>[CH3:8][S:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]2[C:22]([F:23])=[CH:21][C:20]([F:24])=[CH:19][C:18]=2[F:25])=[C:12]([CH2:1][CH:2]([CH3:3])[CH2:6][CH3:7])[N:11]=1Participants
4
Procedure
At 50° C., 70 ml (0.035 mol) of a 0.5 M solution of 2-methylbutylmagnesium bromide (in tetrahydrofuran) were added to 9.1 g (30 mmol) of 2-methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidine (Example 1.1.) and about 200 mg of bisdiphenylphosphinoferrocenepalladium dichloride in 90 ml of toluene. After about 2 hours, an additional about 200 mg of bisdiphenylphosphinoferrocenepalladium dichloride and, a little at a time, a further 50 ml of a 0.5 M solution of 2-methylbutyl-magnesium bromide (in tetrahydrofuran) were added. The reaction was monitored by HPLC.