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Chemical Structure| 400859-08-7 Chemical Structure| 400859-08-7

Structure of 400859-08-7

Chemical Structure| 400859-08-7

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Product Details of [ 400859-08-7 ]

CAS No. :400859-08-7
Formula : C8H5BrN4
M.W : 237.06
SMILES Code : BrC1=CN=C(C2=NC=CC=N2)N=C1

Safety of [ 400859-08-7 ]

Application In Synthesis of [ 400859-08-7 ]

* 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 [ 400859-08-7 ]

[ 400859-08-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 45695-56-5 ]
  • [ 114078-88-5 ]
  • [ 400859-08-7 ]
YieldReaction ConditionsOperation in experiment
9.0 g In 1,4-dioxane; at 0 - 30℃; for 2.0h; To a solution of <strong>[114078-88-5]5-bromotriazine</strong> (20.0 g, crude) in 1,4-dioxane (600 mL) was added pyrimidine-2-carboxamidine (16.8 g, 137.53 mmol) at 0 C. After being stirred at 0 C for 1 hrs, the resulting mixture was warmed to 30 C and stirred at 30 C for 1 hr, and then filtered. The filtrate was concentrated in vacuo. The residue was diluted with H20 (500 mL) and extracted with DCM (500 mL) for three times. The combined organic layer was washed with brine (1.0 L), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified on silica gel column (eluting with DCM/MeOH= 10/1, v:v) to give 5-bromo-2-pyrimidin-2-yl-pyrimidine (9.0 g) as yellow solid.
  • 2
  • [ 82771-60-6 ]
  • [ 400859-08-7 ]
  • 7-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro-l /-isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
26 mg With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; caesium carbonate; In 1,4-dioxane; at 120℃; for 48h;Inert atmosphere; To a mixture of 7-chloro- l,2,3,4-tetrahydroisoquinoline (200 mg, 1.19 mmol), 5-bromo-2- pyrimidin-2-yl-pyrimidine (226 mg, 954 muiotaetaomicron, the product of step 3 in Example 1) and CS2CO3 (1.94 g, 5.97 mmol) in dioxane (15 mL) was added Brettphos Pd G3 (216 mg, 239 muiotaetaomicron, CAS registry number: 1470372-59-8). The resulting mixture was heated at 120 C with stirring for 48 hrs under N2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give 7-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (0436) (26 mg) as light yellow solid. XH NMR (400 MHz, Methanol-^) delta ppm: 8.87-8.99 (m, 2H), 8.55- 8.70 (m, 2H), 7.45-7.59 (m, IH), 7.25-7.38 (m, IH), 7.21 (s, 2H), 4.62 (s, 2H), 3.76 (t, 2H), 3.02 (s, 2H). MS obsd. (ESI+) [(M+H)+] : 324
  • 3
  • [ 33537-99-4 ]
  • [ 400859-08-7 ]
  • 6-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro-1H-isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
10 mg With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos; In 1,4-dioxane; at 110℃; A mixture of 5-bromo-2-pyrimidin-2-yl-pyrimidine (150 mg, 633 muiotaetaomicron, the product of step 3 in Example 1), 6-chloro-l,2,3,4-tetrahydroisoquinoline (127 mg, 759 muiotaetaomicron), Ruphos (11.8 mg, 25.3 muiotaetaomicron), Pd2(dba)3 (11.6 mg, 12.7 muiotaetaomicron) and sodium iert-butoxide (122 mg, 1.27 mmol) in dioxane (10 mL) was heated at 110 C with stirring overnight. After being cooled to rt, the resulting mixture was diluted with H20 and extracted with EA (50 mL) for three times. The combined EA layer was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (10 mg) as light yellow solid. XH NMR (400 MHz, CDC13) delta ppm: 2.99 - 3.08 (m, 2 H), 3.72 (s, 2 H), 4.55 (s, 2 H), 7.15 - 7.20 (m, 1 H), 7.23 (s, 2 H), 7.31 - 7.36 (m, 1 H), 8.60 (s, 2 H), 8.96 (d, 2 H). MS obsd. (ESI+) [(M+H)+] : 324.
 

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