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Chemical Structure| 917896-02-7 Chemical Structure| 917896-02-7

Structure of 917896-02-7

Chemical Structure| 917896-02-7

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Product Details of [ 917896-02-7 ]

CAS No. :917896-02-7
Formula : C10H14BrN3
M.W : 256.14
SMILES Code : CC1=NC=C(Br)C(NC2CCCC2)=N1

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Application In Synthesis of [ 917896-02-7 ]

* 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 [ 917896-02-7 ]

[ 917896-02-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 917896-02-7 ]
  • [ 51376-06-8 ]
  • 5-(2,1,3-benzoxadiazol-5-yl)-N-cyclopentyl-2-methylpyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% Example 49: 5-(2,1,3-benzoxadiazol-5-yl)-/V-cyclopentyl-2-methylpyrimidin-4-amine:; In a flask under argon were placed 200 mg (1.00 mmles, 1.0 eq.) of 5-bromo-2,1,3- benzoxadiazole, 326 mg (1.10 mmoles, 1.10 eq.) of bis(pinacolato)diboron, 986 mg (3.32 mmoles, 3.30 eq.) of AcOK, and 8 mg (0.01 mmoles, 0.01 eq.) of PdCI2(dppf). 3.5 mL of anhydrous DMF were added and the mixture was stirred at 800C for 6h. It was cooled to RT and 170 mg (0.66 mmoles, 0.66 eq.) of 5-bromo-Lambda/-cyclopentyl-2-methylpyrimidin-4-amine, 8 mg (0.01 mmoles, 0.01 eq.) of PdCI2(dppf) were added followed by a solution of 352 mg (3.32 mmoles, 3.30 eq.) of Na2CO3 in 1.41 mL of water. The mixture was heated at 800C for 15h. The experiment was allowed to cool to RT. The solution was partitioned between 35 mL of water and 15 mL of AcOEt. The aqueous phase was extracted two more times with 15 mL of AcOEt. The combined organic layers were washed once with 15 mL of brine, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified by flash chromatography on silica gel. The crude compound was then recrystallized in 1 mL of hot MeOH. The solution was cooled to RT, evaporated to the half and left overnight in the fridge. EPO <DP n="79"/>The solid was filtered off, washed with 2 ml. of Et2O and dried under high vacuum to give 34 mg of a yellow solid. Yield : 11 % M.P. : 165-167C LC-MS : Tr = 3.61 min. (100 %) (ES-MS: m/z 296.2 (M+H)) [Column : Nucleosil C-18HD, 4x70 mm, 3mum, gradient CH3CN/H2O/TFA 0.05% : 20-100% CH3CN (6 min.), 100% CH3CN (1.5 min.), flow : 1 mL/min].1H-NMR (CDCI3, 400 MHz) delta : 1.34-1.45 (m, 2H) ; 1.62-1.74 (m, 4H) ; 2.08-2.17 (m, 2H) ; 2.59 (s, 3H) ; 4.52 (quint, J = 7.0 Hz, 1H) ; 4.80 (d, J = 7.0 Hz, 1H) ; 7.42 (d, J = 9.5 Hz, 1H) ; 7.84 (s, 1H) ; 7.96 (d, J = 9.5 Hz, 1H) ; 8.04 (s, 1H).13C-NMR (CDCI3, 100 MHz) delta : 23.9 ; 26.1 ; 32.9 ; 52.2 ; 114.2 ; 115.5 ; 117.7 ; 132.9 ; 138.7 ; 148.4 ; 149.3 ; 153.9 ; 158.4 ; 168.1.
 

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