Aluminium lithium hydride → 1,6-Dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 1241440노트

반응식

HRID 1241440 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:13][C:12](=O)[NH:11][C:10]2[N:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:9]1=2>C1COCC1>[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:9]1=2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 219345241,6-Dimethyl-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one

생성물 1

HCID 219345911,6-Dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

LiAlH4 (214 mg, 5.64 mmol) was slowly added to 10 mL anhydrous THF in a round-bottom flask fitted with a stir bar and a condenser. After stirring for 10 minutes, a solution of 1,6-dimethyl-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (500 mg, 2.82 mmol) in 5 mL anhydrous THF was added drop wise. Upon completion of the addition, the reaction mixture was refluxed for 16 hours. The reaction was cooled to room temperature and quenched with 1 M NaOH solution until the mixture had become a milky yellow color. The precipitate was filtered off and washed 3 times with CH2Cl2. The filtrate and washings were combined, washed with brine, dried over MgSO4. Filtered and concentrated under reduced pressure to give the desired product as light yellow oil, which solidified on standing. (420 mg, 91% yield). H NMR (CDCl3) δ 2.27 (s, 3H), 2.80 (s, 3H), 3.17 (t, 2H), 3.58 (m, 2H), 6.36 (d, 1H), 6.56 (d, 2H).

후처리

  1. customfitted with a stir bar and a condenser
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was refluxed for 16 hours
  4. customquenched with 1 M NaOH solution until the mixture
  5. filtrationThe precipitate was filtered off
  6. washwashed 3 times with CH2Cl2
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationFiltered
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f1876f763bfa411882ade8d491415a8b
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115596B2

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