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m-Chloroperbenzoic acid → 4-(8-Methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 1010884
ノート
印刷プレビュー

反応式

HRID 1010884 の反応式
[CH3:1][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](SC)[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13][N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 673147444-(8-Methylimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile

生成物 1

HCID 1317290024-(8-Methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

300 mg of the compound [1-6] was dissolved in 6 mL of chloroform, and 368 mg of m-chloroperbenzoic acid was added thereto under an ice-cold condition. After the 30 minutes stirring at the same temperature, to the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, then the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 3 mL of chloroform, poured onto 3 mL of a tetrahydrofuran solution containing 257 mg of S-(−)-1-(4-bromophenyl)ethylamine and 224 μL of triethylamine, and the mixture was stirred overnight at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1), to obtain 252 mg of 2-{[(1S)-1-(4-bromophenyl)ethyl]amino})-4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile [3-1] (hereinafter, referred to as the compound [3-1]) as a pale yellow oily product.

後処理

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 3 mL of chloroform
  6. additionpoured onto 3 mL of a tetrahydrofuran solution
  7. additioncontaining 257 mg of S-(−)-1-(4-bromophenyl)ethylamine and 224 μL of triethylamine
  8. stirringthe mixture was stirred overnight at room temperature
  9. additionTo the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate
  10. extractionthe mixture was extracted with chloroform
  11. washThe obtained organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationThe insolubles were filtered
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

出典と根拠

ORDレコード
ord-e1822a146df94628b0137935254f39f1
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977336B2

反応ノート

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