Sodium hydride → 3-(Cyanopentyl)-7-methylxanthine

HRID 992380

반응식

HRID 992380 반응식
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7](=[O:12])[NH:6][C:5]=2[N:4]=[CH:3]1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22]>CS(C)=O>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:6]1[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[C:9](=[O:11])[NH:8][C:7]1=[O:12])#[N:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 683747-MethylxanthineHCID 810936-Bromohexanenitrile

생성물 1

HCID 228882753-(Cyanopentyl)-7-methylxanthine수율 15.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirring slurry of 2.69 g 7-methylxanthine (16.2 mmol) (Aldrich, Milwaukee, Wis.) in 50 ml methyl sulfoxide was added 0.39 g sodium hydride (16.2 mmol). After 1 hour, 2.85 g of 6-bromocapronitrile (16.2 mmol) (Lancaster Synthesis, Inc., Windham, N.H.) was added neat and the reaction was stirred for 72 h at room temperature. The mixture was then quenched with 150 mL water and extracted five times with 35 ml methyl acetate. The combined extracts were washed two times with 40 ml saturated aqueous sodium bicarbonate solution and two times with 40 ml saturated aqueous sodium chloride solution and then dried over sodium sulfate. After concentration under vacuum, the residual white powder was recrystallized with ethyl acetate-hexane solution to yield 0.64 g 3-(cyanopentyl)-7-methylxanthine (15% yield) as a white solid.

후처리

  1. customThe mixture was then quenched with 150 mL water
  2. extractionextracted five times with 35 ml methyl acetate
  3. washThe combined extracts were washed two times with 40 ml saturated aqueous sodium bicarbonate solution and two times with 40 ml saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe residual white powder was recrystallized with ethyl acetate-hexane solution

출처 및 근거

ORD 기록
ord-f742a5c71eac4eac9ed962676c044553
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469017B1

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