2,4-Dihydroxythieno[2,3-d]pyrimidine synthesis
- Product Name:2,4-Dihydroxythieno[2,3-d]pyrimidine
- CAS Number:18740-38-0
- Molecular formula:C6H4N2O2S
- Molecular Weight:168.17
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18740-38-0
Methyl 2-aminothiophene-3-carboxylate (95 g) and dichloromethane (2.85 L) were added to a 5 L reaction flask fitted with a mechanical stirrer, an internal temperature probe, and a nitrogen bubbler, and the mixture was cooled to -60 °C. Chlorosulfonyl isocyanate (89.81 g) was slowly added while maintaining the internal temperature at -60°C to -55°C. After addition, the reaction mixture was allowed to gradually warm up to room temperature. The reaction was monitored by LC/MS until the feedstock was completely consumed. The reaction mixture was concentrated to dryness under vacuum and the solid residue was transferred to a 5L reaction flask with water (1.8L). The mixture was heated at 75 °C for 1 h and then cooled to 30 °C. Subsequently, 10M NaOH aqueous solution (200mL) was added and the mixture was heated at 85°C for 20 minutes and then cooled to room temperature. The mixture was acidified to pH=1 with concentrated hydrochloric acid and stirred at room temperature for 18 hours, during which time a precipitate formed. The solid was collected by vacuum filtration and the filter cake was washed with water (3 x 300 mL). The solid was dried in a vacuum oven at 55 °C for 24 h to afford thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione as an off-white solid (80.05 g, 78.8% yield).1H NMR (400 MHz, DMSO-d6) δ 7.083 (d, J=5.6 Hz, 1H), δ 7.124 (d, J=5.6 Hz , 1H); LCMS (ESI pos) m/e 169 (M+1).
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Yield: 94%
Reaction Conditions:
with 1,5-diazabicyclo[4.3.0]non-5-ene 2,2,2-trifluoroethanol at 90; for 48 h;
Steps:
8 Example 8 Synthesis of Compound 2h
Compound 1h (1 mmol, 124 mg), [HDBN+][TFE-] (6 mmol, 1.35 g) was added to a 10 ml round bottom flask. In a CO2 environment, the reaction was heated to 90°C for 48 hours, the reaction was stopped, the temperature was cooled to room temperature, and a saturated aqueous solution of NH4Cl was added. Adjust the pH to neutral, extract three times with 20ml CH2Cl2, collect the CH2Cl2 solution and dry it over anhydrous sodium sulfate. After filtration, the solution was removed by evaporation under reduced pressure, and the resulting solid was separated by silica gel column chromatography (eluent: CH2Cl2:CH3OH=15:1).158 mg of a pale yellow solid compound for 2 h, yield 94%.
References:
Guizhou Medical University;Li Chun;Zhang Lin;Yang Yuanyong CN107698587, 2018, A Location in patent:Paragraph 0051; 0052; 0053
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18740-38-0
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18740-38-0
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