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Structure of 514816-42-3

Chemical Structure| 514816-42-3

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Product Details of [ 514816-42-3 ]

CAS No. :514816-42-3
Formula : C6H7BrN2O2
M.W : 219.04
SMILES Code : O=C(C1=C(Br)C=NN1C)OC
MDL No. :MFCD01459850
InChI Key :XOGHZBXSBLBJHQ-UHFFFAOYSA-N
Pubchem ID :673643

Safety of [ 514816-42-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 514816-42-3 ]

* 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 [ 514816-42-3 ]

[ 514816-42-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 84547-84-2 ]
  • [ 514816-42-3 ]
YieldReaction ConditionsOperation in experiment
65.4% With thionyl chloride; for 18.0h;Reflux; <strong>[84547-84-2]4-Bromo-2-methyl-2H-pyrazole-3-carboxylic acid</strong> (6 g, 29.3 mmol) was added to 150 mL of methanol treated with thionyl chloride (3.5 g, 29.3 mmol). The mixture was refluxed for 18 firs. Solvents were evaporated and the residue was extracted with dichloromethane and 0.5N sodium hydroxide solution. The organic layer was washed with brine and dried. After the evaporation of solvents, a white solid (4.19 g, 65.4percent yield) was obtained as the desired compound 4-bromo-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester. 1H NMR (400 MHz, CDC13) delta ppm 3.97 (s, 3H), 4.19 (s, 3H), 7.51 (s, 1H). The aqueous extraction was filtered and neutralized with IN hydrochloric acid. The white solid was filtered and dried to give the unreacted starting material carboxylic acid (1.51 g).
63% Part A. <strong>[84547-84-2]4-bromo-2-methyl-2H-pyrazole-3-carboxylic acid</strong> methyl ester To the suspension of <strong>[84547-84-2]4-Bromo-2-methyl-2H-pyrazole-3-carboxylic acid</strong> (0.205 g, 1 mmol) in methanol (2 mL) was added thionyl chloride (0.29 mL, 4 mmol). The suspension was heated at 90° C. for 18 h to give a clear solution. The solution was cooled to rt and then concentrated. The residue was dissolved in EtOAc (10 mL), and washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give 0.137 g (63percent) of the methyl ester as a white solid. 1H NMR (400 MHz, CDCl3) delta: 3.95 (s, 3H), 4.17 (s, 3H), 7.53 (s, 1H). HRMS calc'd for C6H8BrN2O2: 218.9769. Found: 218.9770.
  • 2
  • [ 514816-42-3 ]
  • [ 1801-06-5 ]
  • methyl 4-(5-fluoro-2-methoxypyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
<Step 1> Synthesis of methyl 4-(5-fluoro-2-methoxypyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate Using 4-bromo-1-methyl-1H-pyrazole-5-carboxylic acid methyl ester (CAS No.: 514816-42-3, 2.52 g, 11.5 mmol) and <strong>[1801-06-5]4-chloro-5-fluoro-2-methoxypyrimidine</strong> (1.5 g), methyl 4-(5-fluoro-2-methoxypyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate (1.6 g) was obtained as a pale yellow liquid using a method similar to that in <Step 1> in Working Example 3 or a method based on this method. (Physical property data) LC-MS: M=266, RT=0.91 (min), [M+H]+=267. 1H-NMR (300 MHz, CDCl3, delta ppm): 8.35 (1H, d, J=2 Hz), 7.86 (1H, d, J=1 Hz), 4.15 (3H, s), 4.00 (3H, s), 3.86 (3H, s).
 

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[ 514816-42-3 ]

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Related Parent Nucleus of
[ 514816-42-3 ]

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