Potassium tert-butoxide → 2-bromo-5H-pyrrolo[2,3-b]pyrazine

HRID 68660

반응식

HRID 68660 반응식
CC(C)([O-])C.[K+].[Br:7][C:8]1[N:9]=[C:10]([C:15]#[C:16][Si](CC)(CC)CC)[C:11]([NH2:14])=[N:12][CH:13]=1>CN1CCCC1=O.CCOC(C)=O.O>[Br:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:16][NH:14][C:11]2=[N:12][CH:13]=1

참가 물질

6

반응물 2

HCID 23665647Potassium tert-butoxideHCID 866757025-Bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine

생성물 1

HCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine수율 70.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매2회HCID 13387N-methyl-2-pyrrolidone용매2회

반응 조건

온도
80 °C

실험 절차

Potassium tert-butoxide (6.612 g, 58.92 mmol) was suspended/dissolved in dry N-methylpyrrolidinone (15 mL) and stirred at 80° C. while a solution of 5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine (9.1992 g, 29.46 mmol) in dry N-methylpyrrolidinone (50 mL) was added slowly drop wise over 10 minutes. The dropping funnel was washed out with a further aliquot of dry N-methylpyrrolidinone (10 mL). The resultant was stirred at 80° C. for 1.5 hours. Reaction mixture cooled to ambient then diluted with EtOAc and water and EtOAc layer washed with small portions of water (×6). Organic layer dried (MgSO4), filtered and concentrated in vacuo to give a dark brown solid (4.1 g, 70.3%). 1H NMR (400.0 MHz, DMSO) δ 12.50 (s, 1H), 8.37 (s, 1H), 8.01 (s, 1H) and 6.64 (q, J=1.7 Hz, 1H) ppm; MS (ES+) 198.10.

후처리

  1. additionwas added slowly drop wise over 10 minutes
  2. washThe dropping funnel was washed out with a further aliquot of dry N-methylpyrrolidinone (10 mL)
  3. customReaction mixture
  4. temperaturecooled
  5. washwashed with small portions of water (×6)
  6. dry with materialOrganic layer dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0ff2bc3b68aa4673910b8a5cd4c05079
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822469B2

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