2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidine → 2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine

HRID 1724650Notes

Reaction equation

HRID 1724650 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]=1

Participants

4

Reactant 2

HCID 575608392-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidineHCID 178445864HCID 178445864, compound2×

Product 1

HCID 575608382-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Sources & evidence

ORD record
ord-2e7420369a7040809a817f5ef4bd8004
Source dataset
uspto-grants-2009_02
Patent number
US07488732B2

Reaction notes

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