A kind of thienopyrimidinone thioglycolic acid derivative and its preparation method and application
A technology for pyrimidone thioglycolic acid derivatives and its derivatives, which is applied in the field of thienopyrimidinone thioglycolic acid derivatives and their preparation, and can solve problems such as poor effect and toxic side effects
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Embodiment 1
[0044] Embodiment 1. Preparation of intermediate 1-cyclopropyl-4-isothiocyanatonaphthalene (b)
[0045] Preparation of intermediate 4-cyclopropyl-1-naphthylamine (a):
[0046] The raw material 4-bromo-1-naphthylamine (3.0g, 13.50mmol) was mixed with cyclopropylboronic acid (1.5g, 17.55mmol) and placed in a 250mL double-necked bottle, and then K was added to the bottle. 3 PO 4 (10.2g, 47.10mmol), tetrakistriphenylphosphine palladium (1.5g, 1.35mmol), after mixing, add about 60mL toluene and 5mL water as solvent, seal, carry out N 2protection, 100°C heating and reflux reaction for 12h; TLC monitoring, after the reaction was completed, the reaction solution was cooled to room temperature, filtered, washed with ethyl acetate (20mL×3), the filtrate was collected, and then the filtrate was dried to obtain a dark brown residue. Add about 30 mL of water to the residue, extract with ethyl acetate (40 mL×3), combine the organic phases, add an appropriate amount of anhydrous magnesium ...
Embodiment 2
[0050] Example 2. Preparation of intermediate 3-(4-cyclopropylnaphthalen-1-yl)-2-mercaptothieno[3,2-d]pyrimidin-4(3H)-one (I-1a)
[0051] Intermediate b (0.507g, 2.25mmol) and methyl 3-aminothiophene-2-carboxylate (0.307g, 1.95mmol) were dissolved in 20mL of absolute ethanol, and heated under reflux at 90°C for 4h; TLC monitoring showed that the reaction was complete After cooling to room temperature, crystals were precipitated, filtered, and the filter cake was taken, then added a small amount of ethanol for recrystallization, filtered to remove the solid, then added 30mL 2mol / L KOH solution, heated to reflux at 90°C until the compound was dissolved, stopped heating, cooled to room temperature, At this time, a small amount of floc was precipitated, and then the pH was adjusted to about 3 with 3mol / L HCl, and a large amount of white solid was precipitated. At this time, it was slowly filtered, washed with water (10mL×2), and dried to obtain intermediate I-1a, which was White s...
Embodiment 3
[0052] Example 3. Intermediate 3-(4-cyclopropylnaphthalen-1-yl)-2-mercapto-7-methylthieno[3,2-d]pyrimidin-4(3H)-one (I-1b ) preparation
[0053] Intermediate b (0.224g, 0.99mmol) and reactant 3-amino-5-methylthiophene-2-carboxylate (0.135g, 0.79mmol) were dissolved in about 5mL of pyridine solution, heated at 45°C for 12h, TLC monitoring, after the reaction is complete, cool to room temperature, add about 40mL of ice water, then extract with dichloromethane (40mL×3), combine the organic phases, dry over anhydrous magnesium sulfate, filter, take the filtrate, evaporate to dryness, and use 30mL of 1% NaOH solution was heated to reflux at 90°C for 12h, cooled to room temperature, filtered, and the filtrate was taken, and the pH was adjusted to about 3 with 1mol / L hydrochloric acid, a large amount of white solid was precipitated, filtered, and the filter cake was washed with water, The intermediate I-1b was obtained as a white solid with a yield of 53.0%; melting point: >250°C; ...
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