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Chemical Structure| 1217501-53-5 Chemical Structure| 1217501-53-5

Structure of 1217501-53-5

Chemical Structure| 1217501-53-5

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Product Details of [ 1217501-53-5 ]

CAS No. :1217501-53-5
Formula : C11H16BNO5S
M.W : 285.12
SMILES Code : O=S(C1=CC=C(B(O)O)C(C)=C1)(N2CCOCC2)=O
MDL No. :MFCD13195673
InChI Key :NHJXSFKMSZWBNM-UHFFFAOYSA-N
Pubchem ID :53216352

Safety of [ 1217501-53-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501

Application In Synthesis of [ 1217501-53-5 ]

* 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 [ 1217501-53-5 ]

[ 1217501-53-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1217501-53-5 ]
  • [ 1612287-81-6 ]
  • 2
  • [ 1217501-53-5 ]
  • [ 1612287-83-8 ]
  • 3
  • [ 59489-71-3 ]
  • [ 1217501-53-5 ]
  • [ 1612287-82-7 ]
YieldReaction ConditionsOperation in experiment
74% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 100.0℃; for 6.0h;Schlenk technique; Inert atmosphere; General procedure: An oven dried resealable Schlenk tube was charged with 5-bromo-2-chloro-1H-pyrrolo[2,3-b]pyridine (Preparation 1c, 0.5 g, 2.07 mmol), (6-methoxy-4-methylpyridin-3-yl)boronic acid (Preparation 2, 0.35 g, 2.08 mmol), cesium carbonate (2.027 g, 6.22 mmol), 5.5 ml dioxane and 5.5 ml water. The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.085 g, 0.10 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 100 C. After 6h, the mixture was cooled and the solvent was removed in vacuo. Water was added and product was extracted with dichloromethane and organic layer was dried (Na2SO4). The residue was purified by flash chromatography (10%, dichloromethane-methanol) to give the title compound (0.353 g, 62% yield) as a solid. LRMS (m/z):274 (M+1)+. 5-Bromopyrazin-2-amine was treated with (2-methyl-4-(morpholinosulfonyl)-phenyl)boronic acid, cesium carbonate, [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane and dioxane as a solvent according to the method described in Preparation 3a. The crude was purified by flash chromatography (0% to 100%, hexane-ethyl acetate) to give the title compound (74% yield). LRMS (m/z): 335 (M+1)+
  • 4
  • [ 1217501-53-5 ]
  • 8-ethyl-6-(2-methyl-4-morpholinosulfonyl-phenyl)-2-methylsulfinyl-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
  • 5
  • [ 1217501-53-5 ]
  • 8-ethyl-6-(2-methyl-4-morpholinosulfonyl-phenyl)-2-[2-(1-methyl-4-piperidyl)ethylamino]pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
  • 6
  • [ 1232030-55-5 ]
  • [ 1217501-53-5 ]
  • 8-ethyl-6-(2-methyl-4-morpholinosulfonyl-phenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
255.3 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium dihydrogenphosphate; In 1,4-dioxane; N,N-dimethyl-formamide; at 120.0℃; under 760.051 Torr; for 0.666667h;Inert atmosphere; Microwave irradiation; Step 1 A 20-mL microwave vial was charged with 6-bromo-8-ethyl-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-one (1.0 equiv, 0.9994 mmol, 300.0 mg), (2-methyl-4-morpholinosulfonyl-phenyl)boronic acid (CASRN 1217501-53-5; 1.50 equiv, 1.499 mmol, 427.4 mg), dibasic potassium phosphate (3.0 equiv, 2.998 mmol, 522.2 mg), (dppf)Cl2Pd(II) (0.10 equiv, 0.09994 mmol, 73.86 mg), degassed DMF (3.7 mL), and degassed 1,4-dioxane (3.7 mL). The reaction mixture was thrice vacuum purged and refilled with N2. The vial was capped, and the reaction mixture was irradiated in microwave at 120 C. for 40 min. The reaction mixture was diluted with EtOAc then filtered through a pad of diatomaceous earth. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated, then purified by SiO2 chromatography eluting with 20 to 100% EtOAc in heptane to afford 255.3 mg of 8-ethyl-6-(2-methyl-4-morpholinosulfonyl-phenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-one as a beige foam. LC-MS m/z: 461.0 [M+1]+. 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.68-7.61 (m, 2H), 7.59 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 4.56 (q, J=7.0 Hz, 2H), 3.79-3.72 (m, 4H), 3.10-3.04 (m, 4H), 2.67 (s, 3H), 2.32 (s, 3H), 1.38 (t, J=7.1 Hz, 3H).
 

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Technical Information

Categories

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