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Chemical Structure| 300816-22-2 Chemical Structure| 300816-22-2

Structure of 300816-22-2

Chemical Structure| 300816-22-2

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Product Details of [ 300816-22-2 ]

CAS No. :300816-22-2
Formula : C9H7ClN2S
M.W : 210.68
SMILES Code : ClC1=C(C2=C(CCC2)S3)C3=NC=N1
MDL No. :MFCD00572400

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Application In Synthesis of [ 300816-22-2 ]

* 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 [ 300816-22-2 ]

[ 300816-22-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 300816-22-2 ]
  • [ 192130-34-0 ]
  • [ 1388893-06-8 ]
  • 2
  • [ 300816-22-2 ]
  • [ 192130-34-0 ]
  • [ 1388893-08-0 ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate; In isopropyl alcohol;Reflux; Example 123. N-(2-(piperazin-l-yl)ethyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[:d]pyrimidin-4-amine. (1-147)Synthesis of tert-butyl 4-(2-((6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4- yl)amino)ethyl)piperazine-l-carboxylate.A mixture of compound D (189 mg, 0.9 mmol, 1 eq) and compound 1 (200 mg, 0.9mmol, 1 eq) in 5 mL of isopropanol was added K2CO3 (248 mg, 1.8 mmol, 2 eq). The reaction mixture was heated at reflux overnight. The mixture was poured into 30 mL of water and extracted with DCM (20 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SC>4 and concentrated. The residue was purified by column chromatography on silica gel(DCM/MeOH = 20/1) to give tert-butyl 4-(2-((6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3- d]pyrimidin-4-yl)amino)ethyl)piperazine-l-carboxylate as white solid (100 mg, 25percent).Synthesis of Compound 1-147.A mixture of Compound 2 (100 mg, 0.25 mmol, 1 eq) in MeOH/HCl (2N, 3ml) was stirred at rt for 12h. The solvent was removed under vacuum and the residue was purified by Prep-HPLC to give N-(2-(piperazin- 1 -yl)ethyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-arnine as a yellow solid (62 mg, 82percent). NMR (400 MHz, D20) delta 2.25-2.29 (m, 2H), 2.72-2.79 (m, 4H), 3.26-3.34 (m, 1 1 H), 3.80 (t, J = 6.0 Hz, 1H), 8.24 (s, 1H). LC/MS calcd for C,5H2iN5S: 303.15. Found: 304.1.
  • 3
  • [ 300816-22-2 ]
  • [ 99337-98-1 ]
  • [ 1388890-61-6 ]
YieldReaction ConditionsOperation in experiment
77% Synthesis of 2-(trans-4-((6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin- 4-yl)hydroxycyclohexyl)isoindoIine-l,3-dione. To a solution of 2-(4- hydroxycyclohexyl)isoindoline-l ,3-dione (837 mg, 3.42 mmol, 1.2 eq) in 20 mL of THF was added NaH ( 137 mg, 3.42 mmol, 60% in oil, 1.2 eq) in one portion at room temperature. The resulting mixture was heated at reflux for 2 hours and cooled down. Compound D (600 mg, 2.85 mmol, 1.0 eq) was added to the mixture as solid in one portion. The reaction was stirred for additional 30 minutes at room temperature. The reaction was quenched with water carefully and extracted with EtOAc (50 mLx3). The combined organics was dried over anhydrous Na2S04 and filtered. The filtrate was concentrated and the residue was purified by column chromatography in silica gel (eluent with DCM) to give 2-(trans-4-((6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3- d]pyrimidin-4-yl)hydroxycyclohexyl)isoindoline-l ,3-dione as white solid ( 1.16g, 77%). MS: m z 420.1 (M+H)+.
 

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