Benzyl Chloride → [9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile

HRID 1399134노트

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HRID 1399134 반응식
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[C:20]([CH3:28])=[N:21][C:22]([O:26][CH3:27])=[N:23][C:24]=4[CH3:25])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:29]O)=[CH:8][CH:7]=1.[C-:31]#[N:32].[Na+].C(Cl)C1C=CC=CC=1>O1CCCC1.C(=O)([O-])O.[Na+].O.CS(C)=O.N1C=CC=CC=1>[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[C:20]([CH3:28])=[N:21][C:22]([O:26][CH3:27])=[N:23][C:24]=4[CH3:25])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH2:29][C:31]#[N:32])=[CH:8][CH:7]=1

참가 물질

10

반응물 4

HCID 7503Benzyl ChlorideHCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 57786330[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

생성물 1

HCID 57786008[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile수율 97%

시약·촉매·용매 5

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

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온도
0 °C

실험 절차

Thionyl chloride (0.56 mL, 7.65 mmol) was added to a stirred solution of [9-chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (1.43 g, 3.83 mmol) and pyridine (0.10 mL) in tetrahydrofuran (20 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. 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. A solution of sodium cyanide (375 mg, 7.65 mmol) in water (1.0 mL) was added to the resulting benzyl chloride in dimethylsulfoxide (20 mL), and the mixture was stirred at room temperature for 14 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and the precipitate was collected by filtration, washed with diisopropyl ether to give the title compound as a colorless powder (1.42 g, 3.71 mmol, 97% in 2 steps).

후처리

  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. stirringthe mixture was stirred at room temperature for 14 hr
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diisopropyl ether

출처 및 근거

ORD 기록
ord-b2b5b88f5bfd41958bb54eb2046af3c3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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