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Chemical Structure| 73-68-7 Chemical Structure| 73-68-7

Structure of 73-68-7

Chemical Structure| 73-68-7

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Product Details of [ 73-68-7 ]

CAS No. :73-68-7
Formula : C6H7N3O
M.W : 137.14
SMILES Code : O=CC1=CN=C(C)N=C1N
MDL No. :MFCD09864101
InChI Key :NOHYIPRJOCCNMG-UHFFFAOYSA-N
Pubchem ID :12904726

Safety of [ 73-68-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Application In Synthesis of [ 73-68-7 ]

* 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 [ 73-68-7 ]

[ 73-68-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 698-29-3 ]
  • [ 73-68-7 ]
YieldReaction ConditionsOperation in experiment
83% With formic acid; nickel; In water; for 0.25h;Reflux; (0273) To a solution of the compound of Reference Example 22 (50.0 g, 373 mmol) in formic acid (150 mL) were added water (65 mL) and Raney nickel (50 g). The mixture was heated under reflux for 15 minutes, cooled to room temperature, and filtrated through Celite, and then 28% ammonia water (220 mL) was added thereto under ice cooling. The mixture was stirred under ice cooling for 1 hour, and the precipitate was collected by filtration. The filter cake was washed with water (30 mL) and chloroform (30 mL×2), and dried in vacuo. Furthermore, the filtrate was extracted with chloroform (200 mL) nine times, and the combined organic layer was concentrated. The resulting concentrated residue and the above-obtained filter cake were mixed, chloroform (70 mL) was added thereto, the mixture was stirred at room temperature for 30 minutes, hexane (210 mL) was added dropwise thereto over 10 minutes, and the mixture was stirred at room temperature for additional 1 hour. The precipitate was collected by filtration, washed with hexane/chloroform (3/1, 28 mL), and dried in vacuo to give the title compound (42.6 g, 83%). 1H-NMR (400 MHz, CDCl3) delta: 2.57 (3H, s), 5.98 (1H, brs), 8.15 (1H, brs), 8.57 (1H, s), 9.86 (1H, s).
83% With formic acid; In water; for 0.25h;Reflux; Compound of Reference Example 22 (50.0g, 373mmol) was added to the formic acid solution (150mL) and water (65mL) Raney nickel (50g). After heating to reflux for 15 min, cooled to room temperature, filtered through celite, under ice-cooling 28% aqueous ammonia (220 mL) was added, after stirring for 1 hour under ice-cooling, the precipitate was collected by filtration. The filtrate quality goods and washed with water (30 mL) and chloroform (30 mL × 2 times) followed by drying under reduced pressure. Further, the filtrate was extracted 9 times with chloroform (200 mL), the organic layer was concentrated. The combined quality goods braze obtained this concentrated residue before, chloroform (70 mL) was added, after stirring for 30 minutes at room temperature, hexane (210 mL) was added dropwise over 10 minutes, further stirred at room temperature for 1 hour. Thereafter, the precipitate was collected by filtration, washed with hexane / chloroform (3 / 1,28mL), the title compound was dried under reduced pressure (42.6g, 83%) was obtained.
70% With sulfuric acid; palladium 10% on activated carbon; hydrogen; In water; at 20℃; for 16h; To a solution of 51 (700 mg, 5.2 rnrnoi) in water and H2S04 is added Pd/C (10 wt. %, 543 mg). After stirring at room temperature under hydrogen for 16 hours, the mixture is filtered through a. pad of? Celite and washed with water. The filtrate is treated with ammonium hydroxide, and the solid is collected by filtration and dried to give 52 (500 mg, 70%). (MS: [M±HI 1381)
58.5% 4-Amino-2-methylpyrimidine-5-carbonitrile (500 mg, 3.73 mmol) and 10% palladium on carbon (40.8 mg, 38.3 mumol) were combined in water (4 mL) and sulfuric acid (800 muL). The mixture was hydrogenated at room temperature and 30-50 psi for 75 minutes. The reaction mixture was filtered through Celite and washed with water. The filtrate was combined with the washes and treated with concentrated ammonium hydroxide. Solid precipitated out of solution, with heat given off. The mixture was chilled prior to collecting the solid by filtration. The filtered solid was washed with water and then dried under house vacuum to give 4-amino-2-methylpyrimidine-5-carbaldehyde. (Yield 299.2 mg, 2.18 mmol, 58.5%).
With formic acid; at 80℃; for 4h; A solution of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong> 1a (3.04g, 30mmol) and raney nickel (3.0g) in formic acid (20mL) was stirred at 80C for 4h. After this, the reaction mixture was filtered and washed with 10mL formic acid. The filtrate and washings were collected together and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and eluted with ethyl acetate/petroleum ether (1:1, v/v) to give white solid 2a, which was used directly for the next step. Under this same condition, the intermediate compounds 2a and 2c were also prepared.

  • 2
  • [ 73-68-7 ]
  • [ 326-62-5 ]
  • [ 76574-68-0 ]
  • 3
  • [ 73-68-7 ]
  • [ 67197-53-9 ]
  • [ 76574-83-9 ]
  • 4
  • [ 64-18-6 ]
  • [ 698-29-3 ]
  • [ 73-68-7 ]
  • 5
  • [ 698-29-3 ]
  • [ 7440-44-0 ]
  • [ 73-68-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; formic acid;aluminum nickel; In water; hydrogen; Method A 6-(2,6-Dichlorophenyl)-2-methylpyrido[2,3,-d]-pyrimidin-7-amine A mixture of 76.5 g of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong>, 380 ml of 97% formic acid, 380 ml of water, and 8 g of Raney nickel catalyst is treated in a Parr pressure apparatus with hydrogen gas at an initial pressure of 51 psi at room temperature for 2.75 hours. The catalyst is removed by filtration and the filtrate is treated with 47.5 ml of concentrated hydrochloric acid and evaporated at reduced pressure. The residue is dissolved in hot water, treated with charcoal and filtered. Neutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which is then collected by filtration and washed with water. Recrystallization from ethanol gives 37.9 g of 4-amino-2-methylpyrimidine-5-carboxaldehyde, mp 191-192.5 C.
 

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