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Chemical Structure| 1609259-55-3 Chemical Structure| 1609259-55-3

Structure of 1609259-55-3

Chemical Structure| 1609259-55-3

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Product Details of [ 1609259-55-3 ]

CAS No. :1609259-55-3
Formula : C13H14N2O
M.W : 214.26
SMILES Code : OC1=CC=C(C2=C(C)N=CN=C2C)C(C)=C1
MDL No. :MFCD30471105

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Application In Synthesis of [ 1609259-55-3 ]

* 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 [ 1609259-55-3 ]

[ 1609259-55-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1609259-55-3 ]
  • [ 220939-72-0 ]
  • [ 1609581-30-7 ]
YieldReaction ConditionsOperation in experiment
53% With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h; 3-Bromo-4-chlorofuro[3,2-c]pyridine (C39, prepared according to the method of Y. Miyazaki et al., Bioorg. Med. Chem. Lett. 2007, 17, 250-254; 430 mg, 1.85 mmol), 4-(4,6- dimethylpyrimidin-5-yl)-3-methylphenol (C38) (396 mg, 1.85 mmol) and cesium carbonate (1.21 g, 3.71 mmol) were combined in dimethyl sulfoxide (8.0 mL) and heated at 120 00 for 3 hours.The reaction mixture was filtered through Celite, the Celite pad was rinsed thoroughly with ethyl acetate, and the combined filtrates were washed twice with a 1:1 mixture of water and saturated aqueous sodium chloride solution, then washed twice with 1 N aqueous sodium hydroxide solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatographic purification (Gradient: 50% to 90% ethyl acetate in heptane) affordedthe product as a white solid. Yield: 404 mg, 0.985 mmol, 53%. LCMS m/z 412.0 (M+H). 1H NMR (400 MHz, ODd3) oe 8.98 (s, 1H), 8.07 (d, J=5.9 Hz, 1H), 7.69 (s, 1H), 7.26-7.28 (m, 1H, assumed; partially obscured by solvent peak), 7.25 (d, J=5.9 Hz, 1 H), 7.21-7.25 (m, 1 H), 7.09 (br d, J=8.2 Hz, 1 H), 2.28 (s, 6H), 2.05 (br s, 3H).
  • 2
  • [ 918340-51-9 ]
  • [ 1609259-55-3 ]
  • 4-[4-(4,6-dimethylpyrimidin-5-yl)-3-methylphenoxy]furo[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h; Step 6. Synthesis of ' 4-[4-{4^-dimethyipynmidin-5-yi)-3-methyiphenoxy]furo[2,3- djpyrimidine (1). To a stirred solution of C3 (33 mg, 0.21 mmol) in dimethyl sulfoxide (1 ml_) was added C5 (45 mg, 0.21 mmol) and cesium carbonate (205 mg, 0.63 mmol). The reaction mixture was stirred at 120 C for 3 hours, then was cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified via silica gel chromatography (Gradient: 0% to 40% [80:20: 1 dichloromethane / methanol / concentrated ammonium hydroxide] in dichloromethane) to provide the product as a pale yellow solid. Yield: 30 mg, 0.09 mmol, 43%. LCMS m/z 333.1 [M+H]+. 1 H NMR (400 MHz, CDCI3) delta 8.96 (s, 1 H), 8.55 (s, 1 H), 7.76 (d, J=2.3 Hz, 1 H), 7.19 (m, 1 H), 7.10 (m, 1 H), 6.79 (d, J=2.5 Hz, 1 H), 2.24 (s, 6H), 2.03 (s, 3H), 1.51 (s, 3H).
 

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