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CAS No. : | 16490-02-1 | MDL No. : | MFCD00094473 |
Formula : | C6H4N2O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | XIEOKRXVAACBHI-UHFFFAOYSA-N |
M.W : | 168.11 | Pubchem ID : | 239360 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
Dimethyl pyrimidine-4,6-dicalpharboxylalphate (llalpha)To a heated solution (75C) of 4,6-dimethylpyrimidine (846 mg, 8.00 mmol) and NaOH (211 mg, 5.28 mmol) in water (3 mL) was added a solution OfKMnO4 (5.28 g in 25 mL water) overl5 min. The resulting mixture was stirred at 80C for 3 hrs. The hot solution was filtered hot and manganese dioxide washed with hot water (8 mL). The filtrate and washings were concentrated to 5 mL and acidified with cone. HCl to pH 2-3. After cooling, the precipitation was collected, yielding 591 mg of crude pyridine-4,6-dicarboxylic acid. The diacid was then dissolved in MeOH (15 mL) and cone. H2SO4 (1.5 mL) was added dropwise carefully. The mixture was refluxed for 24 hrs, cooled to room temperature and concentrated in vacuo. The resultant oily residue was neutralised with sat. NaHCO3 and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with H2O (50 mL) and brine (5OmL), dried over Na2SO4, filtered and concentrated. The product was then purified by column chromatography (petroleum ether 40-60 : EtOAc 5 : 5 to 3 :7) yielding 311 mg (20%) of 11 a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Another embodiment of the invention are compounds selected from: ... Pyrimidine-4,6-dicarboxylic acid, bis-[(1,3-benzodioxol-5-ylmethyl)-amide]; Pyrimidine-4,6-dicarboxylic acid, bis-(4-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, bis-(3-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, bis-(4-carboxy-benzylamide); and Pyrimidine-4,6-dicarboxylic acid, bis-(4-carbomethoxy-benzylamide). | ||
A compound selected from: ... Pyrimidine-4,6-dicarboxylic acid bis-(1,3-benzodioxol-5-ylmethyl) ester, Pyrimidine-4,6-dicarboxylic acid, bis-(4-chloro-benzylamide); Pyrimidine-4,6-dicarboxylic acid, bis-[(1,3-benzodioxol-5-ylmethyl)-amide], Pyrimidine-4,6-dicarboxylic acid bis-(4-methoxy-benzylamide), Pyrimidine-4,6-dicarboxylic acid, bis-(3-methoxy-benzylamide), Pyrimidine-4,6-dicarboxylic acid, bis-(4-carboxy-benzylamide), and Pyrimidine-4,6-dicarboxylic acid. bis-(4-carbomethoxy-benzylamide) | ||
The combination according to Embodiment 50, wherein the compound of Formula IF is selected from: ... Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (4-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carbomethoxy-benzylamide), (3-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-pyridylmethylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-thiophenemethylamide); Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzothiadiazol-5-ylmethyl) amide, [(1,3-benzodioxol-5-ylmethyl)-amide]; Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzooxadiazol-5-ylmethyl) amide, [(1,3-benzodioxol-5-ylmethyl)-amide]; Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzothiadiazol-5-ylmethyl) amide, (4-methoxy-benzylamide); ... |
The combination according to Embodiment 50, wherein the compound of Formula IF is selected from: ... Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (4-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carbomethoxy-benzylamide), (3-methoxy-benzylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-pyridylmethylamide); Pyrimidine-4,6-dicarboxylic acid, (4-carboxy-benzylamide), (3-thiophenemethylamide); Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzothiadiazol-5-ylmethyl) amide, [(1,3-benzodioxol-5-ylmethyl)-amide]; Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzooxadiazol-5-ylmethyl) amide, [(1,3-benzo ioxol-5-ylmethyl)-amide]; Pyrimidine-4,6-dicarboxylic acid, (2,1,3-benzothiadiazol-5-ylmethyl) amide, (4-methoxy-benzylamide); ... | ||
With potassium permanganate; | Intermediate 8: pyrimidine-4,6-dicarboxylic acidPrepared by the KMnO4 oxidation of 2,6-dimethylpyrimidine according to the procedure described in J. Chem. Soc. 525 (1959). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; at 85℃; for 2h; | 200mg(1.2 mmol) of <strong>[16490-02-1]pyrimidine-4,6-dicarboxylic acid</strong> were suspended in 0.3ml(4.1mmol) of thionyl chloride. This mixture was heated at 85C for 2h while being stirred. After it had been cooled down to room temperature, 2ml of absolute dichloromethane were added. The suspension was cooled down to 0C and 0.33ml(2.4mmol) of triethylamine was added. 861mg(5.4mmol) of 3-chloro-4-fluorobenzylamine were added while stirring vigorously. The mixture was then stirred for further 15 minutes. It was then diluted with 10ml of dichloromethane after which 10ml of water were added. After 5 minutes, the mixture was transferred into a separating funnel and the phases were separated. The organic phase was washed twice with saturated sodium chloride solution and then dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue which was obtained in this way was dissolved in ethyl acetate. The product was crystallized from the solution by adding heptane. Beige-colored flakes were obtained and were dried under reduced pressure. Yield: 263mg (49%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.4% | With hydrogenchloride; In water; at 65℃; for 3h;Heating / reflux; | 10g (0.059 mol) of pyrimidine-4,6-dicarboxylic acid were suspended in 1.4 l of methanol, after which 10.93 ml (0.356 mol) of concentrated hydrochloric acid were added and the mixture was stirred under reflux (65C) for 3 hours (h). The reaction mixture was concentrated under reduced pressure after which the residue was taken up once again in methanol; the mixture was filtered and the resulting solution was concentrated.[0121] Yield 11.02 g (94.4%) MS (ES +): m/e = 197.20 |
79% | With thionyl chloride; at 0℃; for 5h;Inert atmosphere; Reflux; | SOCl2 (4.76 g, 4 mmol) was added to a solution of pyrimidine-4, 6-dicarboxylic acid (3.40 g, 2 mmol) in MeOH (250 mL) at 0C. The mixture was heated under reflux and stirred for 5 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was diluted with saturated aqueous NaHC03 (100 mL), and extracted with EtOAc (100 mL> |
With sulfuric acid; for 24h;Reflux; | Dimethyl pyrimidine-4,6-dicalpharboxylalphate (llalpha)To a heated solution (75C) of 4,6-dimethylpyrimidine (846 mg, 8.00 mmol) and NaOH (211 mg, 5.28 mmol) in water (3 mL) was added a solution OfKMnO4 (5.28 g in 25 mL water) overl5 min. The resulting mixture was stirred at 80C for 3 hrs. The hot solution was filtered hot and manganese dioxide washed with hot water (8 mL). The filtrate and washings were concentrated to 5 mL and acidified with cone. HCl to pH 2-3. After cooling, the precipitation was collected, yielding 591 mg of crude pyridine-4,6-dicarboxylic acid. The diacid was then dissolved in MeOH (15 mL) and cone. H2SO4 (1.5 mL) was added dropwise carefully. The mixture was refluxed for 24 hrs, cooled to room temperature and concentrated in vacuo. The resultant oily residue was neutralised with sat. NaHCO3 and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with H2O (50 mL) and brine (5OmL), dried over Na2SO4, filtered and concentrated. The product was then purified by column chromatography (petroleum ether 40-60 : EtOAc 5 : 5 to 3 :7) yielding 311 mg (20%) of 11 a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; triethylamine; In N-methyl-acetamide; dichloromethane; toluene; | Example 1 Pyrimidine 4,6-dicarboxylic acid di-(2-methoxyethyl)-amide (formula I: R1 =CH2 -CH2 -OCH3; R2 =H) 1.7 g of <strong>[16490-02-1]pyrimidine-4,6-dicarboxylic acid</strong> are suspended in 20 ml of toluene, and 2.4 g of thionyl chloride and 0.2 ml of dimethylformamide are added. The mixture is heated to the reflux temperature until no further evolution of gas is to be observed (about 3 hours). About 5 ml of solvent are distilled off, the mixture is cooled to 0-10 C. and 1.9 g of 2-methoxyethylamine and 2.8 ml of triethylamine, dissolved in 10 ml of toluene, are added. The solution is heated slowly to room temperature, stirred at room temperature for 12 hours and evaporated to dryness. The residue is taken up in 50 ml of methylene chloride, the mixture is extracted 3 times by shaking with saturated sodium bicarbonate solution and the organic phase is washed with water, dried with magnesium sulfate and evaporated. The solid is recrystallized from diisopropyl ether. Yield: 2.1 g; melting point: 85-86 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The compound is prepared analogously to Example 12 from <strong>[16490-02-1]pyrimidine-4,6-dicarboxylic acid</strong> di-(3-methoxypropy--1)-amide (Example 5). |
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