Triacetoxyperiodinane → 1-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-one

HRID 1399056ノート

反応式

HRID 1399056 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([CH:45]([OH:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1>C(#N)C.C(=O)([O-])O.[Na+]>[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([C:45](=[O:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 44156374HCID 44156374、化合物

生成物 1

HCID 577863001-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-one収率 88%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Dess-Martin reagent (1.27 g, 3.00 mmol) was added to a stirred suspension of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (1.12 g, 2.73 mmol) in acetonitrile (23 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, concentrated in vacuo, and extracted with ethyl acetate/tetrahydrofuran. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with diisopropyl ether to give the title compound as a colorless powder (980 mg, 2.40 mmol, 88%).

後処理

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with diisopropyl ether

出典と根拠

ORDレコード
ord-370834d74e624712b0d3ce01b402244f
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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