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Chemical Structure| 1032757-58-6 Chemical Structure| 1032757-58-6

Structure of 1032757-58-6

Chemical Structure| 1032757-58-6

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Product Details of [ 1032757-58-6 ]

CAS No. :1032757-58-6
Formula : C19H26ClN5O3S
M.W : 439.96
SMILES Code : C[C@H](O)C(N1CCN(CC2=C(C)C3=NC(Cl)=NC(N4CCOCC4)=C3S2)CC1)=O

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Application In Synthesis of [ 1032757-58-6 ]

* 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.

  • Upstream synthesis route of [ 1032757-58-6 ]

[ 1032757-58-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1032757-58-6 ]
  • [ 1173206-16-0 ]
  • [ 1032754-93-0 ]
YieldReaction ConditionsOperation in experiment
10 mg With bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 100 - 150℃; Alkaline conditions The HCl salt of 2-chloro-7-methyl-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidine (590 mg) was reacted with lactic acid via General Procedure B-2 to give (S)-1-(4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one.
References: [1] Patent: US9335320, 2016, B2, . Location in patent: Paragraph 76; 77.
  • 2
  • [ 402960-38-7 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
YieldReaction ConditionsOperation in experiment
10 mg With bis-triphenylphosphine-palladium(II) chloride In acetonitrile The Suzuki-type coupling reaction is useful to attach a monocyclic heteroaryl at the 2-position of the pyrimidine ring (see Scheme 4). Generally, substituted 2-chloro-4-morpholinothieno[3,2-d]pyrimidine 5 or substituted 2-chloro-4-morpholinothieno[2,3-d]pyrimidine 6 may be combined with 1.5 equivalents of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 7a, and dissolved in 3 equivalents of sodium or potassium carbonate as a 1 molar solution in water and an equal volume of acetonitrile. A catalytic amount, or more, of a low valent palladium reagent, such as bis(triphenylphosphine)palladium(II) dichloride, is added. A variety of boronic acids or boronic esters can be used in place of the pinacol boronic ester indicated. Also alternatively, the nitrogen of the pyrimidin-2-amine may be protected, for example with a tetrahydropyranyl group. In some cases potassium acetate was used in place of sodium carbonate to adjust the pH of the aqueous layer. The reaction was then heated, for example to about 100-150° C. under pressure in a Biotage Optimizer microwave reactor (Biotage, Inc.) for 10 to 30 minutes. The contents are extracted with ethyl acetate, or another organic solvent. After evaporation of the organic layer the product, 8a or 9a, may be purified on silica or by reverse phase HPLC. (S)-1-(4-((2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one (60 mg) was reacted with 50 mg of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A-2 to give 10 mg of Formula Ib (WO 2008/070740, incorporated by reference).
References: [1] Patent: JP5658565, 2015, B2, . Location in patent: Paragraph 0286; 0366; 0369.
  • 3
  • [ 936250-22-5 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
References: [1] Organic Process Research and Development, 2015, vol. 19, # 3, p. 416 - 426.
  • 4
  • [ 71-23-8 ]
  • [ 936250-22-5 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
References: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column.
  • 5
  • [ 71-23-8 ]
  • [ 936250-22-5 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
References: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column.
 

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