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Chemical Structure| 71819-06-2 Chemical Structure| 71819-06-2

Structure of 71819-06-2

Chemical Structure| 71819-06-2

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Product Details of [ 71819-06-2 ]

CAS No. :71819-06-2
Formula : C10H11IN4O
M.W : 330.13
SMILES Code : IC1=C2N=CN(C3CCCCO3)C2=NC=N1

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Application In Synthesis of [ 71819-06-2 ]

* 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 [ 71819-06-2 ]

[ 71819-06-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 71819-06-2 ]
  • [ 63558-65-6 ]
  • [ 1093101-61-1 ]
YieldReaction ConditionsOperation in experiment
6-Iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (620 mg, 1878 mumol) was dissolved in THF (1 mL) in a 15 mL microwave tube and sealed. The solution was flushed with argon and then cooled to -40 C. A solution of isopropylmagnesium chloride (2254 mul, 2254 mumol) (LiCl complex, 1 N in THF) was added in dropwise slowly. The reaction was allowed to stirred at -40 0C for 15 min, LCMS showed incompletioin of Mg-I exchange. The mixture was warmed to rt, LCMS indicated Mg-I exchange was still not completed, and then the mixture was cooled to -40 0C again and a solution of isopropylmagnesium chloride-LiCl complex (1 N in THF, ImL) was added again in dropwise via a syringe. The reaction mixture was stirred at this temperature for 20 min (LCMS showed all starting material consumed). Under -40 0C, a solution of zinc chloride, 0.5 M in THF (4883 mul, 2441 mumol) was added in dropwise. Another 2 mL of the zinc chloride solution was added in to counter the additional Mg reagent. The mixture was stirred at this temperature for 1 hr and gradually warmed to RT. This solution was poured into a solution of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong> (429 mg, 1784 mumol), tris(dibenzylideneacetone)dipalladium (0) (103 mg, 1 13 mumol), and tri-2-furylphosphine <n="79"/>(105 mg, 451 mumol) (TFP) in THF (15 mL) flushed with argon. This reaction mixture was heated to 60 0C under argon for 16 hours. The reaction mixture was cooled to rt and quenched with NH4Cl (aq., sat., 10 mL) and partitioned between H2O and EtOAc, 40 mL each. The organic was collected, and filtered through a layer of silica gel. The silica layer was rinsed with THF (80 mL). The filtrate was combined and concentrated. The residue was loaded on silica gel and purified via flash column on silica (A: hexane, B: 1 : 1 THF/EtOAc, B:A=5-40%). Desired fractions were collected and concentrated to give a dark brown gel. This brown gel was precipitated with hexane:EtOAc=l:l to give a light brown solid. This solid was washed with the same solvent once and then dried in the air to give 6-(4-chloropyrimidin-5-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine. MS Found: (ESI pos. ion) m/z 317 (M+H+).
 

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