A kind of preparation method of 4,6-dichloro-2-(propylthio)pyrimidin-5-amine
A technology of propylthio and pyrimidine, which is applied in the field of preparation of 4,6-dichloro-2-pyrimidin-5-amine, can solve the problems of expensive and difficult to obtain catalysts, unsuitable for industrial production, complex preparation methods, etc., to achieve reaction The effect of short time, cheap reagents and easy operation
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Embodiment 1
[0044] Preparation of 2-propylthio-4,6-dihydroxypyrimidine (9)
[0045] 2-Thiobarbituric acid (compound 8, 20 g) was added to water (50 mL) with stirring. Weigh sodium hydroxide (12.6g) and dissolve it in water (29.4mL), add dropwise to the above mixture under ice bath, keep the temperature at 20~25°C, stir at this temperature for 40 minutes, then add water (40mL ), then the temperature was raised to 32°C, at this temperature, n-propane iodide (24.6g) dissolved in methanol (40mL) was added, and the reaction solution was stirred at 32°C for 30 hours. Use dilute hydrochloric acid to adjust the pH value of the reaction solution to below 2, and then after the reaction at 32°C, filter and wash the filter cake with water (2*40mL). The filter cake was refluxed in cyclohexane for 30 minutes, cooled to room temperature, filtered, and dried under reduced pressure at 45°C to obtain 21.91 g of compound (9), with a yield of 84.9%. m / z (M-H) 185.
[0046] 1H-NMR (DMSO-d6) δ: 0.95 (3H, t)...
Embodiment 2
[0057] Preparation of 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (1)
[0058] Add the ethanol (2mL) solution of compound (11) (0.5g) in the there-necked flask, get sodium dithionite (0.97g) and add NaHCO 3 (0.15 g) in water (5 mL), the mixture of sodium dithionite was added dropwise to the solution of compound (11) at 0-5°C. Stir the reaction for 1 hour and pass through the diatomite cake, wash the filter cake with ethyl acetate, separate the layers, extract the aqueous phase with ethyl acetate (3*5mL), combine the organic phases, wash with water (3*5mL), and concentrate under reduced pressure After drying, 0.36 g of oily compound (1) was obtained (yield 80.8%, HPLC purity 96.8%).
Embodiment 3
[0060] Preparation of 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (1)
[0061] Add compound (11) (0.5g) in tetrahydrofuran (2mL) solution in the there-necked flask, get sodium dithionite (3.25g) and add NaHCO 3 (0.4 g) in water (5 mL), the mixture of sodium dithionite was added dropwise to the solution of compound (11) at 5-10°C. Stir the reaction for 15 minutes and pass through the diatomite cake, wash the filter cake with ethyl acetate, separate the layers, extract the aqueous phase with ethyl acetate (2*5mL), combine the organic phases, wash with water (2*5mL), and concentrate under reduced pressure After drying, 0.37 g of oily compound (1) was obtained (yield 83.3%, HPLC purity 98.2%).
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