反応 #91400

反応方程式

5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one

phosphorus (V) oxychloride

→

titled compound

収率 74.0%

4-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine

収率 74.0%

反応条件

後処理

1. 1
   温度was refluxed overnight under nitrogen
2. 2
   その他Then excess phosphorus (V) oxychloride was removed under reduced pressure
3. 3
   workup.ADDITIONToluene (30 mL) was added
4. 4
   その他the reaction mixture was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was diluted with 5% aqueous sodium bicarbonate (100 mL)
6. 6
   抽出extracted with ethyl acetate (2×200 mL)
7. 7
   その他The solvent was evaporated under reduced pressure
8. 8
   洗浄eluted with hexane/ethyl acetate (2:1)

実験手順

A solution of 5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one (7.0 g, 32.6 mmol, Step B) in phosphorus (V) oxychloride (30 mL) with addition of 1 drop of dimethylformamide was refluxed overnight under nitrogen. Then excess phosphorus (V) oxychloride was removed under reduced pressure. Toluene (30 mL) was added, and the reaction mixture was evaporated under reduced pressure. The residue was diluted with 5% aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×200 mL). The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography eluted with hexane/ethyl acetate (2:1). The titled compound 6.1 g (74%) was obtained as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.10 (s, 3H), 2.39 (s, 3H), 4.54 (s, 2H), 7.20-7.30 (m, 2H), 7.68-7.76 (m, 2H), 7.76 (bs, 1H).

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