Chloromethyl methyl sulfide → 1-methylsulfanylmethyl-4-(2-methyl-4-m-tolylethynyl-imidazol-1-yl)-1H-pyridin-2-one

HRID 2194451Notes

Reaction equation

HRID 2194451 reaction equation
[CH3:1][C:2]1[N:3]([C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=2)[CH:4]=[C:5]([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)[N:6]=1.[H-].[Na+].Cl[CH2:26][S:27][CH3:28]>CN(C)C=O>[CH3:26][S:27][CH2:28][N:19]1[CH:20]=[CH:21][C:16]([N:3]2[CH:4]=[C:5]([C:7]#[C:8][C:9]3[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=3)[N:6]=[C:2]2[CH3:1])=[CH:17][C:18]1=[O:22]

Participants

5

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 498726724-(2-Methyl-4-m-tolylethynyl-imidazol-1-yl)-1H-pyridin-2-one

Product 1

HCID 668650391-methylsulfanylmethyl-4-(2-methyl-4-m-tolylethynyl-imidazol-1-yl)-1H-pyridin-2-oneYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.35 mmol) of 4-(2-Methyl-4-m-tolylethynyl-imidazol-1-yl)-1H-pyridin-2-one in 0.5 ml of dimethylformamide were added 17 mg (0.42 mmol, 1.2 equiv.) of a 60% sodium hydride suspension in mineral oil. After stirring for 1 h at room temperature, 40 uL (50 mg, 0.52 mmol, 1.5 equiv.) of chloromethyl methylsulfide were added and the suspension was stirred for another 16 h at room temperature. After workup with methylene chloride/water, the crude material was purified by flash chromatography (SiO2, gradient ethyl acetate to ethyl acetate:methanol 90:10 v/v) to yield 32 mg of the title compound as a light yellow solid, MS: 350.2 (M+H+).

Workup

  1. stirringthe suspension was stirred for another 16 h at room temperature
  2. customAfter workup with methylene chloride/water, the crude material was purified by flash chromatography (SiO2, gradient ethyl acetate to ethyl acetate:methanol 90:10 v/v)

Sources & evidence

ORD record
ord-10ecc634088d4a049559a964ea58332d
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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