反応 #837908

反応方程式

2-(3-Cyano-4-methyl-6-trifluoromethanesulfonylpyridin-2-ylmercapto)acetamide

sodium carbonate

methyl 2-butynoate

dimethylamine

ammonium chloride

→

title compound

収率 45.0%

3-Amino-6-dimethylamino-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide

収率 45.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度the reaction heated at 100° C. for 6 h
2. 2
   温度cooled to room temperature overnight
3. 3
   抽出extracted with EtOAc
4. 4
   抽出The organic extract
5. 5
   洗浄was washed with brine
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他to afford 23.0 mg of the crude product
10. 10
    その他This was purified via automated flash silica chromatography (4 g silica gel column, 30-100% EtOAc/hexanes)

実験手順

2-(3-Cyano-4-methyl-6-trifluoromethanesulfonylpyridin-2-ylmercapto)acetamide (30.0 mg, 0.08 mmol) (prepared as described in Example 1 for the n-propyl analog but using methyl 2-butynoate) and dimethylamine (170.0 microL, 0.34 mmol) were mixed in 1,4-dioxane (0.5 mL) in a pressure tube and heated at 80° C. for 1 h. 2.0 M Aqueous sodium carbonate (520 μL, 1.04 mmol) was added, and the reaction heated at 100° C. for 6 h, then cooled to room temperature overnight. The mixture was poured into saturated aqueous ammonium chloride, and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 23.0 mg of the crude product. This was purified via automated flash silica chromatography (4 g silica gel column, 30-100% EtOAc/hexanes) to afford 9.0 mg (0.02 mmol, 45% yield) of the title compound.

出典