* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1 N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea. To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
With sodium carbonate; In water; at 25 - 30℃; for 12h;
Diethyl 2-(ethoxymethylene)malonate compound of formula-2 (100 g) was added to a mixture of 2-methyl-2-pseudothiourea sulfate compound of formula-3 (77.24 g) and water (300 ml) at 25-30C. Sodium carbonate solution (98.04 g of sodium carbonate in 300 ml of water) was slowly added to the reaction mixture at 25-30C and stirred for 12 hours at the same temperature. After completion of the reaction, quenching the reaction mixture with dilute hydrochloric acid and stirred for 1 hour at 15-20C. Filtered the precipitated solid and washed with water to obtain title compound. This wet solid taken into next step.
Take 50g (231.4mmol) diethyl ethoxymalonate to the three-neck flask, add 100ml of absolute ethanol, 32g (115.7mmol) S-methylisothiourea sulfate, 13.8g sodium hydroxide at room temperature,Heat to reflux for 2 hours, cool to room temperature, concentrate and evaporate the ethanol, add 200ml of water, 2N hydrochloric acid adjusted PH=3-4, precipitate a white solid, and filter to obtain ethyl 4-hydroxy-2-methylthiopyrimidine-5-carboxylate 40.6 g, yield 82%, purity: 99.7%.
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