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Chemical Structure| 873651-92-4 Chemical Structure| 873651-92-4

Structure of 873651-92-4

Chemical Structure| 873651-92-4

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Product Details of [ 873651-92-4 ]

CAS No. :873651-92-4
Formula : C6H8N2O
M.W : 124.14
SMILES Code : OCC1=NC=C(N)C=C1
MDL No. :MFCD07368188
InChI Key :FLSFZTQIYGDVFB-UHFFFAOYSA-N
Pubchem ID :20583240

Safety of [ 873651-92-4 ]

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

Application In Synthesis of [ 873651-92-4 ]

* 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 [ 873651-92-4 ]

[ 873651-92-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 323578-38-7 ]
  • [ 873651-92-4 ]
  • 2
  • [ 24242-20-4 ]
  • [ 873651-92-4 ]
YieldReaction ConditionsOperation in experiment
36% With dimethylsulfide borane complex; In tetrahydrofuran;Reflux; To a stirred solution of 5-aminopicolinic acid (400 mg, 2.90 mmol) in tetrahydrofuran were added BH3S e2 (2 M in tetrahydrofuran) (4.34 ml_, 8.69 mmol, 3 eq) at room temperature. The reaction mixture was refluxed for overnight. TLC showed complete consumption of starting material. The reaction mixture was quenched with water and extracted with ethylacetate. The organic part was washed with brine. The organic layer was dried over MgS0 and concentrated under reduced pressure to afford crude product which was purified by column chromatography to afford (5-aminopyridin-2-yl)methanol (136 mg, 36 %).
36% With dimethylsulfide borane complex; In tetrahydrofuran; at 20℃;Reflux; Step 1: To a stirred solution of 5-aminopicolinic acid (400 mg, 2.90 mmol) in tetrahydrofuran were added BH3SMe2 (2 M in tetrahydrofuran) (4.34 mL, 8.69 mmol, 3 eq) at room temperature. The reaction mixture was refluxed for overnight. TLC showed complete consumption of starting material. The reaction mixture was quenched with water and extracted with ethylacetate. The organic part was washed with brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford crude product which was purified by column chromatography to afford (5-aminopyridin-2-yl)methanol (136 mg, 36%).
Preparation of Intermediate 1-20; (5-Amino-2-pyridyl)methanolReagents: (a) LAH, THF, 40 C[0250] Standard Method E; LAH Reduction of Carboxylic Acids was used to prepare the title compound from <strong>[24242-20-4]5-aminopyridine-2-carboxylic acid</strong>; 1H NMR (DMSO-de) delta 7.83 (d, 1H), 7.08 (d, 1H), 6.90 (dd, 1H), 5.16 (br s, 3H), 4.36 (s, 2H).; Standard Method E; LAH Reduction of Carboxylic Acids[0203] A solution of the amide in THF (0.25 M) was treated with LAH (5-10 eq) and the solution heated (from 40 C to reflux). The reaction mixture was stirred for 4-18 h, then cooled in an ice bath. The reaction was quenched by carefully adding n mL of 1 M NaOH(aq) solution, 3 times n mL of H20, and n mL of 1 M NaOH(aq) solution, where n is the number of moles of LAH used. Stirring continued at room temperature for 1 h. The mixture is filtered and the filtrate concentrated under reduced pressure to give the product alcohol.
 

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[ 873651-92-4 ]

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Related Parent Nucleus of
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Pyridines

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