Hydrochloric Acid → 2,2,2-Trifluoro-1-[9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]ethanol

HRID 1399374ノート

反応式

HRID 1399374 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH:44]=[O:45])=[C:25]2[C:29]=1[N:28]=[C:27]1[N:30]([C:34]3[C:35]([CH3:43])=[N:36][C:37]([O:41][CH3:42])=[N:38][C:39]=3[CH3:40])[CH2:31][CH2:32][CH2:33][N:26]21.C[Si](C)(C)[C:48]([F:51])([F:50])[F:49].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[F:49][C:48]([F:51])([F:50])[CH:44]([C:24]1[C:25]2[N:26]3[CH2:33][CH2:32][CH2:31][N:30]([C:34]4[C:35]([CH3:43])=[N:36][C:37]([O:41][CH3:42])=[N:38][C:39]=4[CH3:40])[C:27]3=[N:28][C:29]=2[C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[OH:45]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 577857769-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde

生成物 1

HCID 441565002,2,2-Trifluoro-1-[9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]ethanol収率 40.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 0.13 mL, 0.13 mmol) was added to a stirred solution of the 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (467 mg) and trimethyl(trifluoromethyl)silane (361 mg, 2.54 mmol) in tetrahydrofuran (5.0 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min, at room temperature for 70 min. 1N Hydrochloric acid (5.0 mL) was added to the mixture at room temperature, and the mixture was stirred for 15 min. The mixture was neutralized 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 0-7% methanol/ethyl acetate gradient mixture. The eluate was concentrated in vacuo to give the title compound as a colorless solid (224 mg, 0.512 mmol).

後処理

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with ethyl acetate
  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 0-7% methanol/ethyl acetate gradient mixture
  8. concentrationThe eluate was concentrated in vacuo

出典と根拠

ORDレコード
ord-2b41761bd2e64fb1a6e65dc89bf758f5
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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