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Chemical Structure| 53925-27-2 Chemical Structure| 53925-27-2

Structure of 53925-27-2

Chemical Structure| 53925-27-2

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Product Details of [ 53925-27-2 ]

CAS No. :53925-27-2
Formula : C5H5N3O4
M.W : 171.11
SMILES Code : OC1=NC(C)=NC(O)=C1[N+]([O-])=O
MDL No. :MFCD00193996
InChI Key :MRYKPLCGITXZRW-UHFFFAOYSA-N
Pubchem ID :252478

Safety of [ 53925-27-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 53925-27-2 ]

* 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.

  • Downstream synthetic route of [ 53925-27-2 ]

[ 53925-27-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1194-22-5 ]
  • [ 53925-27-2 ]
YieldReaction ConditionsOperation in experiment
15% With nitric acid; at 0 - 20℃; for 3h; [00858] 4,6-Dihydroxy-2-methylpyrimidine (1.0 g, 7.9 mmol) was added gradualy to ice-cooled fuming nitric acid (3 ml) stirring. The mixture was stirred for 2 hours cooling with ice and for 1 hour at the room temperature, and then the precipitated crystal was filtered and dried to obtain 207 mg (yield 15%) of 4,6-dihydroxy-2-methyl-5-nitropyrimidine.
In nitric acid; Part A: 4,6-Dihydroxy-2-methylpyrimidine (60 g) was added in portions to fuming nitric acid (120 ML) at 0 C. while cooling the reaction flask. After completion of addtion, the reaction was stirred an additional 1 h at 0 C. followed by another 1 h at room temperature. The reaction mixture was then poured over ice (200 g) and the ice was allowed to melt. A light pink solid was isolated by filteration and washed with cold water (100 mL). The solid was dried in a vacuum oven overnight to yield 4,6-dihydroxy-2-methyl-5-nitropyrimidine (72.5 g).
In nitric acid; Part A 4,6-Dihydroxy-2-methylpyrimidine (60 g) was added in portions to fuming nitric acid (120 mL) at 0 C. while cooling the reaction flask. After completion of addition, the reaction was stirred an additional 1 h at 0 C. followed by another 1 h at room temperature. The reaction mixture was then poured over ice (200 g) and the ice was allowed to melt. A light pink solid was isolated by filtration and washed with cold water (100 mL). The solid was dried in a vacuum oven overnight to yield 4,6-dihydroxy-2-methyl-5-nitropyrimidine (72.5 g).
With nitric acid; trifluoroacetic acid; at 0 - 15℃; EXAMPLE lYY"OH 2-methyl-5-nitropyrimidine-4,6-diolPowdered <strong>[1194-22-5]4,6-dihydroxy-2-methylpyrimidine</strong> (9 g, 71 mmol) was dissolved in trifluoroacetic acid (54 mL). The reaction mixture was cooled in ice- water as nitric acid (4.3 mL) was added dropwise over a period of 30 minutes. During addition the internal temperature was maintained below 15 C. After the addition, the cooling was removed and the reaction stirred overnight. Water (50 mL) was added to the reaction mixture and the resulting solid was filtered and dried under vacuum to obtain 2-methyl-5-nitropyrimidine-4,6-diol (5.8 g). 1H NMR (400 MHz, DMSO-J6): delta 12.97(br, 2H), 2.32 (s, 3H). MS (m/z) 172 (M +I)-
With nitric acid; for 0.25h;Cooling with ice; Reference Example 177 4,6-Dihydroxy-2-methyl-5-nitropyrimidine To fuming nitric acid (50 mL) was added <strong>[1194-22-5]4,6-dihydroxy-2-methylpyrimidine</strong> (25 g) slowly under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added ice water (500 mL), and the resulting mixture was stirred at room temperature until the ice melted. The precipitated crystals were collected by filtration. The collected crystals were washed with water, and dried under reduced pressure to give the title compound (26.6 g).
20 g (68%) With nitric acid; trifluoroacetic acid; In water; (a) 2-Methyl-4,6-dihydroxy-5-nitropyrimidine. To a three-necked, round-bottomed flask equipped with an addition funnel, condenser, internal temperature probe and mechanical stirrer was added trifluoroacetic acid (Aldrich Chemical Company) (120 mL, 710 mmol) and powdered 2-methyl-4,6-dihydroxy pyrimidine (Aldrich Chemical Company) (20 g, 160 mmol). The suspension was stirred under a N2 atmosphere for 15 min to allow complete dissolution of the solids. Nitric acid (9.7 mL, 210 mmol, 90% aq soln) was added over 25 min while maintaining the internal temperature between 13-21 C. by cooling the reaction flask in an ice bath. Stirring was continued for 12 h at room temperature. Water (100 mL) was added, and the resulting precipitate was collected by filtration and washed with H2O. Recrystallization from H2O followed by drying in the vacuum oven provided 20 g (68%) of the title compound as a white crystalline solid. 1H NMR (DMSO-d6; 400 MHz): delta 3.9 (s,3). 13C NMR (DMSO-d6; 100.6 MHz): delta 17.94, 118.0, 155.7, 161.7. MS m/z: 170 (M-1).

  • 3
  • [ 1194-22-5 ]
  • 2-(dinitromethylidene)-5,5-dinitrodihydropyrimidine-4,6(1H,5H)-dione [ No CAS ]
  • [ 53925-27-2 ]
  • 4
  • [ 1194-22-5 ]
  • [ 53925-27-2 ]
 

Historical Records

Technical Information

Categories

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[ 53925-27-2 ]

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Related Parent Nucleus of
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