Triacetoxyperiodinane → 9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde

HRID 1629021ノート

反応式

HRID 1629021 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[C:33]2[N:32]=[C:31]3[N:34]([C:38]4[C:39]([CH3:47])=[N:40][C:41]([O:45][CH3:46])=[N:42][C:43]=4[CH3:44])[CH2:35][CH2:36][CH2:37][N:30]3[C:29]=2[C:28]([CH2:48][OH:49])=[CH:27][CH:26]=1>CS(C)=O.C(#N)C.C(=O)([O-])O.[Na+]>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH:48]=[O:49])=[C:29]2[C:33]=1[N:32]=[C:31]1[N:34]([C:38]3[C:39]([CH3:47])=[N:40][C:41]([O:45][CH3:46])=[N:42][C:43]=3[CH3:44])[CH2:35][CH2:36][CH2:37][N:30]21

参加物

6

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 57786030[9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

生成物 1

HCID 577857769-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde収率 61.7%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Dess-Martin reagent (1.31 g, 3.09 mmol) was added to a stirred solution of [9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (761 mg, 2.06 mmol) in dimethyl sulfoxide (0.50 mL) and acetonitrile (8.2 mL) at 0° C., and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. 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 0-5% methanol/ethyl acetate gradient mixture. The eluate was concentrated in vacuo to give the title compound as a brown solid (467 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-5% methanol/ethyl acetate gradient mixture
  7. concentrationThe eluate was concentrated in vacuo

出典と根拠

ORDレコード
ord-b8c865ea6c734ed49b4bdc64fbfe6f1c
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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