Potassium Carbonate → HCID 68690458、化合物

HRID 2238688ノート

反応式

HRID 2238688 の反応式
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:38][F:39])(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:39][CH2:38][O:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 13862289Fluoromethyl 4-methylbenzenesulfonateHCID 68690427HCID 68690427、化合物

生成物 1

HCID 68690458HCID 68690458、化合物収率 39.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

100 mg of the 4-(8-hydroxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [158-1] was dissolved in 3 mL of N,N-dimethylformamide, 146 mg of potassium carbonate and 216 mg of fluoromethyl 4-methylbenzenesulfonate (synthesized according to a method disclosed in page 555 to 566 in J. Labelled Compd. Radio pharm. 2003, 46) were added, and stirred at 80° C. for 5 hours. After cooling the reaction mixture back to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added, and was extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of a mixture solvent of chloroform and methanol (chloroform:methanol=9:1), and solidified by adding diethyl ether, to obtain 44.1 mg of 4-[8-(fluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [160-1] as a brown solid.

後処理

  1. addition2003, 46) were added
  2. temperatureAfter cooling the reaction mixture back to room temperature
  3. extractionwas extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in a small amount of a mixture solvent of chloroform and methanol (chloroform:methanol=9:1)
  9. additionby adding diethyl ether

出典と根拠

ORDレコード
ord-e1536c965c4648c3b8ebd907a0bc2262
出典データセット
uspto-grants-2010_05
特許番号
US07718801B2

反応ノート

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