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Chemical Structure| 1400287-54-8 Chemical Structure| 1400287-54-8

Structure of 1400287-54-8

Chemical Structure| 1400287-54-8

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Product Details of [ 1400287-54-8 ]

CAS No. :1400287-54-8
Formula : C10H8ClN3
M.W : 205.64
SMILES Code : NC1=CC=C(C2=CN=CN=C2)C=C1Cl

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Application In Synthesis of [ 1400287-54-8 ]

* 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 [ 1400287-54-8 ]

[ 1400287-54-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4595-59-9 ]
  • [ 850567-56-5 ]
  • [ 1400287-54-8 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Microwave irradiation; Preparation 134: 2-Chloro-4-(pyrimidin-5-yl)aniline; [00304] To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.1 10g, 0.434 mmol), 5-bromopyrimidine (0.090 g, 0.56 mmol), 1 ,1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (23 mg, 0.028 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1 .06 mmol). The microwave vial was heated at 150C for 15 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (15 mL), dried (Na2S04) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 20% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :5) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :1 ) (2 x 5 mL) and acetone (3 x 4 mL) to give the title compound as a white solid (0.075 g, 84%). 1 H-NMR (500 MHz, DMSO-d6) 5.72 (s, 2H), 6.91 (d, J = 8.4, 1 H), 7.51 (dd, J = 2.2, 8.3 Hz, 1 H), 7.72 (d, J = 2.2 Hz, 1 H), 9.04, 9.05 (2 x s, 3H).
  • 2
  • [ 4595-59-9 ]
  • [ 721960-43-6 ]
  • [ 1400287-54-8 ]
YieldReaction ConditionsOperation in experiment
84% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Microwave irradiation; Preparation 134 2-Chloro-4-(pyrimidin-5-yl)aniline To a mixture of <strong>[721960-43-6]4-amino-3-chlorophenylboronic acid pinacol ester</strong> (0.110 g, 0.434 mmol), 5-bromopyrimidine (0.090 g, 0.56 mmol), 1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) DCM complex (23 mg, 0.028 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1.06 mmol). The microwave vial was heated at 150 C. for 15 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHCO3 solution (15 mL). The organic layer was washed with a saturated aqueous NaHCO3 solution (15 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 20% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 2% MeOH in ethyl acetate/CH2Cl2 (v/v; 1:5) (20 mL). The silica was removed by filtration, washed with ethyl acetate/CH2Cl2 (v/v; 1:1) (2*5 mL) and acetone (3*4 mL) to give the title compound as a white solid (0.075 g, 84%). 1H-NMR (500 MHz, DMSO-d6) 5.72 (s, 2H), 6.91 (d, J=8.4, 1H), 7.51 (dd, J=2.2, 8.3 Hz, 1H), 7.72 (d, J=2.2 Hz, 1H), 9.04, 9.05 (2*s, 3H).
 

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