Structure of 18740-38-0
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CAS No. : | 18740-38-0 |
Formula : | C6H4N2O2S |
M.W : | 168.17 |
SMILES Code : | OC1=NC(O)=C(C=CS2)C2=N1 |
MDL No. : | MFCD11520884 |
InChI Key : | JGOOQALRLGHKIY-UHFFFAOYSA-N |
Pubchem ID : | 12217323 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With trichlorophosphate; In N,N-dimethyl-formamide; at 115℃; for 8h; | Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (12) (2.5 g, 0.012 mol) and a drop of DMF were added to 20 mL POCl3. Heated to 115 C for 8 h. After cooling to room temperature, the reactant was added to 500 g ice-water mixture slowly. The product was filtered off and dissolved in CH2Cl2. The insoluble was filtered off and the filtrate was distilled under reduced pressure to afford 1.7g 2,4-dichlorothieno[2,3-d]pyrimidine (13). Yield: 56.0 %, 1H NMR (400 MHz, DMSO) delta 8.16 (d, J=3.4 Hz, 1H, Ar-H), 7.62 (d, J=3.4 Hz, 1H, Ar-H). ESI-MS m/z: 205.1. |
56% | With N,N-dimethyl-formamide; trichlorophosphate; at 115℃; for 5h; | To 1 g of dry thieno [2,3-d] pyrimidine-2,4 (1H, 3H) -dione was added 10 g of phosphorus oxychloride,Add 1 drop of DMF catalyst, heating to 115 , the reaction 5h, the reaction is completed, the reaction slowly added to the crushed ice,While stirring vigorously,A brown solid,Filter, filter residue dissolved in 50mL of dichloromethane, to the solution by adding 1g activated carbon and 2g silica gel,Heated to 45 reflux decolorization 1h, while the hot filter, remove the solvent,Pale yellow solid,2,4-dichlorothieno [2,3-d] pyrimidine in a yield of 56.0%. |
56% | With N,N-dimethyl-aniline; trichlorophosphate; In acetonitrile; at 0 - 85℃; for 24h; | Thieno[2,3-d] pyrimidine-2,4 (1H, 3H) -dione (IX-2) (5.0 g, 29.7 mmol)And 3 mL of N, N-dimethylaniline were dissolved in 30 mL of acetonitrile,It was cooled to 0 C.16 mL of phosphorus oxychloride is kept at the reaction temperature not higher than 25 C.I am dripping slowly. The reaction mixture was heated and stirred at 80-85 C. for 24 hours.The reaction solution was cooled to 15 C.,Was slowly added to 70 mL of ice water.The obtained slurry was collected by filtration,And washed with cold water (20 mL).After drying, column chromatography (elution solvent: hexane: dichloroMethane = 1: 2)3.41 g (yield 56%) of the dichloro compound (IIa-2) was obtained as gray crystals. |
49% | 3 g (0.018 mol) of the intermediate lib was placed in a 100 mL three-necked flask,30 mL (0.329 mol) of phosphorus oxychloride was slowly added dropwise,After 30 min addition, 2 drops of DMF were added to the reaction mixture and the reaction was heated to reflux for 8 h. The reaction was poured into 1000 g of ice water with stirring, and a large amount of orange-colored solid was precipitated. The filter cake was washed with a large amount of water and dried at 45 C for 24 hours to obtain 1.8 g of an orange solid in a yield of 49%. | |
41% | With trichlorophosphate; at 106℃; for 3h;Inert atmosphere; | Under a nitrogen streamThieno [2,3-d] pyrimidine-2,4 (1H, 3H) -dione (8.4 g, 50.0 mmol) and phosphoryl chlorideL), which was stirred for 3 hours at 106 C. After completion of the reaction, the organic layer was separated using ethyl acetateWater was removed using MgSO4. The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound2,4-dichlorothieno [2,3-d] pyrimidine (4.2 g, 20.5 mmol, yield 41%). |
40% | With trichlorophosphate; at 116℃; for 3h; | A mixture of thieno[2,3-phiyrimidine-2,4(l//,3//)-dione (100 mg, 0.59 mmol) and phosphonyl chloride (2 mL, 21.5 mmol) was heated at 1 16 0C for 3 h. Upon completion of the reaction, the reaction mixture was poured into ice and extract with ethyl acetate 3 times. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by column chromatography, eluting with Hexanes/Ethyl Acetate (9: 1) afforded the product as a white solid (48.1 mg, 40%): 1H NMR (DMSO, 300 MHz) delta 7.6 (d, J = 6.3 Hz, IH), 8.13(d, J = 5.7 Hz, IH). |
35.5% | With N,N-dimethyl-aniline; trichlorophosphate; for 16h;Reflux; | A total of 0.8 mL N,N-dimethylaniline was added to 3.0 g of thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione 6a in 20 mL POCl3. The mixture was then heated under reflux for 16 h. Excess POCl3 was removed in vacuo, and the resulting residue was treated with ice water to yield a precipitate. The solid was collected by filtration, washed with water and dried over a funnel to afford solid 7a (1.3 g, yield 35.5%). 1H NMR (400 MHz, CDCl3): delta 7.62 (d, J = 6.4 Hz, 1H), 7.43 (d, J = 6.4 Hz, 1H). |
With trichlorophosphate; at 200℃; for 2.3h; | EXAMPLE 402,4-Dichlorothieno[2,3-d]pyrimidine; The dione of Example 39 (2.6 g) was placed into a pressure vessel with phosphorus oxychloride (15 mL). The mixture was heated at 200 0C for 2.3 hours and then cooled to room temperature and concentrated under reduced pressure. Residual phosphorus oxychloride was azeotroped . twice with toluene (30 mL) under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The resulting layers were separated and the organic layer was filtered through anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to give 1.06 g of the title compound: MS (ESI+) for C6H2N2CI2S m/z205.0 (M+H)+. 1H NMR (400 MHz, CDCI3) delta 7.42 (d,1 H), 7.61 (d,1 H). | |
With N,N-dimethyl-aniline; trichlorophosphate; In toluene; at 100℃; for 3h; | To a solution of 1H-thieno[2,3-d]pyrimidine-2,4-dione (62) (92.8 mg, 0.552 mmol) in toluene (1 mL) were added N,N-dimethylaniline (0.140 mL, 1.10 mmol) and phosphoryl chloride (0.280 mL, 3.00 mmol). The reaction mixture was warmed to 100 C and stirred for 3 h. After cooling to room temperature, H2O was added to the reaction mixture and the mixture was extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give 2,4-dichlorothieno[2,3-d]pyrimidine (63). This compound was used for the next reaction without further purification.To a solution of 63 in DMF (4 mL) was added ethyl 2-(4-aminophenyl)acetate (95.2 mg, 0.531 mmol) and the reaction mixture was stirred at 65 C for 2.5 h. After cooling, H2O was added to the reaction mixture and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (EtOAc/hexane = 0% to 100%) to give the title compound (85.9 mg, 0.247 mmol, 45%) as a colorless solid. 1H NMR (CDCl 3) delta: 1.28 (3H, t, J = 7.4 Hz), 3.64 (2H, s), 4.18 (2H, q, J = 7.4 Hz), 7.03 (1H, d, J = 5.7 Hz), 7.21 (1H, s), 7.29 (1H, d, J = 5.7 Hz), 7.32 (2H, d, J = 8.6 Hz), 7.56 (2H, d, J = 8.6 Hz). |
Tags: 18740-38-0 synthesis path| 18740-38-0 SDS| 18740-38-0 COA| 18740-38-0 purity| 18740-38-0 application| 18740-38-0 NMR| 18740-38-0 COA| 18740-38-0 structure
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