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Chemical Structure| 16229-26-8 Chemical Structure| 16229-26-8

Structure of 16229-26-8

Chemical Structure| 16229-26-8

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Product Details of [ 16229-26-8 ]

CAS No. :16229-26-8
Formula : C6H6N4S
M.W : 166.20
SMILES Code : NNC1=C2C(C=CS2)=NC=N1
English Name :4-Hydrazinylthieno[3,2-d]pyrimidine
MDL No. :MFCD01763693

Safety of [ 16229-26-8 ]

Application In Synthesis of [ 16229-26-8 ]

* 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 [ 16229-26-8 ]

[ 16229-26-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 16229-26-8 ]
  • [ 272-68-4 ]
YieldReaction ConditionsOperation in experiment
With oxygen; sodium ethanolate In ethanol
With oxygen
  • 2
  • [ 72934-37-3 ]
  • [ 16229-26-8 ]
  • [ 1073488-46-6 ]
YieldReaction ConditionsOperation in experiment
23% Stage #1: 3-(4-chlorophenyl)-1-cyclopropanecarboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: 4-hydrazinothieno[3,2-d]pyrimidine In tetrahydrofuran at 0 - 20℃; 28 [00130] To a solution of l-(4-chlorophenyl)cyclopropanecarboxylic acid (1.97 g, 10 mmol) in 20 mL of THF was added NMM (1.11 g, 11 mmol). The resulting mixture was cooled to 0 0C and then isobutyl chloroformate (1.37 g, 10 mmol) was added. After 20 minutes at 0 0C, compound 28A (1.66 g, 10 mmol) was added to the resulting white suspension. Upon completion of addition, the reaction mixture was allowed to warm to rt and stirred overnight. EtOAc (300 mL) and water (100 mL) was added. The aqueous layer was removed and the EtOAc layer (which contained the desired product as a precipitate) was washed successively with 100 mL of saturated aqueous sodium bicarbonate, ammonium chloride, and brine. The EtOAc layer (containing a solid precipitate) was filtered and the solid was washed with EtOAc (2x5 mL) to provide compound 28B as a tan powder (805 mg, 23%). LC/MS (m/z) = 345.8 (M+H)+.
  • 3
  • [ 876376-75-9 ]
  • [ 16229-26-8 ]
  • [ 1641559-11-6 ]
  • [ 1641559-17-2 ]
YieldReaction ConditionsOperation in experiment
60% With hydrogenchloride In ethanol at 70℃; for 6h; regioselective reaction; General Procedure for the Preparation of 3A and 3B. General procedure: 4-Hydrazinothienopyrimidine 1A or 1B (10 mmol) and the appropriate (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one 2 (10 mmol) were mixed in ethanol (50 mL) containing HCl (1 eq), and the mixture was heated to 70 °C for 6 h. After evaporation of the solvent, the residue was purified by column chromatography using as eluent CH2Cl2-EtOAc (8:2) to give 3A and 3B, respectively.
60% With hydrogenchloride In ethanol at 70℃; for 6h; General Procedure for the Preparation of 3A and 3B General procedure: 4-Hydrazinothienopyrimidine 1A or 1B (10 mmol) and theappropriate (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one 2 (10 mmol) were mixed in ethanol (50 mL) containingHCl (1 eq), and the mixture was heated to 70 °C for 6 h.After evaporation of the solvent, the residue was purified bycolumn chromatography using as eluent CH2Cl2-EtOAc (8:2)to give 3A and 3B, respectively.
 

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