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Chemical Structure| 934493-81-9 Chemical Structure| 934493-81-9

Structure of 934493-81-9

Chemical Structure| 934493-81-9

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Product Details of [ 934493-81-9 ]

CAS No. :934493-81-9
Formula : C14H15N5OS
M.W : 301.37
SMILES Code : O=C1C(C2=NNC=C2)=CC3=C(C)N=C(SC)N=C3N1CC

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Application In Synthesis of [ 934493-81-9 ]

* 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 [ 934493-81-9 ]

[ 934493-81-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 934493-80-8 ]
  • [ 376584-63-3 ]
  • [ 934493-81-9 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; [00207] To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10:1 11 mL) was added lH-pyrazol-5- ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpprhof),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl- 2-(methylthio)-6-(lH-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J= 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J= 7.2Hz, 3H). EPO <DP n="66"/>
77% With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10: 1 1 1 mL) was added l H-pyrazol-5-ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpppf),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl-2-(methylthio)-6-(lH-pyrazol- 5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J = 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J = 7.2Hz, 3H).
77% With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 20℃; for 4h;Heating / reflux; [00242] To a solution of 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin- 7(8H)-one (0.765 g, 2.43 mmol) in DME-H2O (10:1 11 mL) was added lH-pyrazol-5- ylboronic acid (Frontier, 0.408 g, 3.65 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (Pd(dpppf),0.198 g, 0.243 mmol) and triethylamine (0.736 g, 7.29 mmol) at room temperature. Then the reaction mixture was heated to reflux and reacted for 4 h. After cooling down to room temperature, the reaction mixture was partitioned with water and ethyl acetate. After separation, the organic layer was dried with Na2SO4, and the product 8-ethyl-4-methyl- <n="74"/>2-(methylthio)-6-(lH-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.567 g, 77percent yield) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CDCl3): delta 13.3 (bs, IH), 8.54 (s, IH), 7.82-7.07 (m, 2H), 4.45 (q, J= 7.2 Hz, 2H), 2.71 (s, 3H), 2.60 (s, 3H), 1.26 (t, J= 7.2Hz, 3H).
  • 2
  • [ 934493-81-9 ]
  • [ 934493-76-2 ]
YieldReaction ConditionsOperation in experiment
To the solution of 8-ethyl-4-methyl-2-(methylthio)-6-(lH-pyrazol-5-yl)pyrido[2,3- d]pyrimidin-7(8H)-one (0.123 g, 0.41mmol) in DCM (2 mL) was added MCPBA (0.176 g, 77%, 0.785 mmol) in a small portion at room temperature. Then the reaction mixture was stirred for 4 h. After evaporation of DCM, dioxane (1 mL) and liquid ammonia (1 mL) were introduced. The reaction was stirred at room temperature overnight. The product 2-amino-8- ethyl-4-methyl-6-(lH-pyrazol-5-yl)pyrido[2,3-cT]pyrimidin-7(8H)-one (50.4 mg) was obtained by silica gel column chromatography. 1H NMR (400 MHz, CD3OD): delta 8.41 (s, IH), 7.62 (d, J = 2.0 Hz, IH), 6.96 (d, J = 2.0Hz, IH), 4.51 (q, J = 7.2Hz, 2H), 2.64 (s, 3H), 1.29 (t, J = 7.2Hz, 3H); MS (EI) for Ci3Hi4N6O: 271.3 (MH+).
 

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