Sodium hydride → 2-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 905987노트

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HRID 905987 반응식
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 714334512-bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine

생성물 1

HCID 866423052-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine수율 70.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

2-Bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine (0.300 g, 1.41 mmol) was dissolved in DMF (5 mL) and cooled down to 0° C. NaH (60%, 68 mg, 1.70 mmol) was added slowly. After the addition was complete stirring was continued for 30 minutes at 0° C. (2-Chloromethoxy-ethyl)-trimethyl-silane (0.30 mL, 1.70 mmol) was added and the reaction mixture was allowed to warm up overnight. The reaction was quenched with H2O. The aqueous layer was extracted with EtOAc. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 340 mg of 2-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow liquid (70% yield).

후처리

  1. additionAfter the addition
  2. temperatureto warm up overnight
  3. customThe reaction was quenched with H2O
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc)

출처 및 근거

ORD 기록
ord-f46a3e69f1c04dd38da9b46d9a12bffa
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012974B2

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