Methyl iodide → 2-(6-Chloro-2,5-dimethylpyrimidin-4-yl)-2-(2,4,6-trimethylphenyl)-propionitrile
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:10]#[N:11])[C:3]=1[CH3:21].[CH3:22][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])([CH3:22])[C:10]#[N:11])[C:3]=1[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (6-chloro-2,5-dimethylpyrimidin-4-yl)-(2,4,6-trimethylphenyl)-acetonitrile (0.250 g, 0.834 mmol) in 4ml of dry THF was cooled to −78° C. and treated with lithium bistrimethylsilylamide (1.0 M in THF, 0.92 ml) and stirred at that temperature for 45 minutes. Methyl iodide (0.426 g, 3.00 mmol) was added. The reaction mixture was gradually warmed to room temperature and stirred for 1 hour. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow oil. The oil residue was purified through silica gel chromatotron using ethyl acetate/hexane (4:6) as eluent to give 161 mg (62%) of yellow solid, mp 18-183° C. 1H NMR (CDCl3) δ 6.980 (s, 2H), 3.45 (s, 3H), 2.40 (s, 3H), 2.24 (s, 3H), 2.21 (s, 6H), 1.25 (s, 3H) ppm.
Workup
- stirringstirred for 1 hour
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- customThe organic layer was dried
- concentrationconcentrated
- customto give a yellow oil
- customThe oil residue was purified through silica gel chromatotron
Sources & evidence
- ORD record
- ord-0672eab6b57c4d28be962ccbfe479877
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956047B1
Reaction notes
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