Sodium Methoxide → 8-methoxy-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 527768노트

반응식

HRID 527768 반응식
Br[C:2]1[N:3]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH3:17][C@H:13]([O:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([O:25][CH3:24])[N:3]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[C:8]([NH2:11])[N:7]=1)[CH2:14][CH2:15][CH3:16]

참가 물질

4

반응물 2

HCID 10942334Sodium Methoxide3회HCID 576998418-bromo-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

생성물 1

HCID 576996248-methoxy-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

시약·촉매·용매 1

HCID 887Methanol용매4회

반응 조건

온도
90 °C

실험 절차

8-Bromo-2-{[(1S)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (7.1 g, 18.48 mmol) was dissolved in anhydrous methanol (70 ml) and a solution of sodium methoxide (25%) in methanol (8 ml) was added dropwise under an atmosphere of nitrogen. The solution was heated to reflux at 90° C. for 4 hours under an atmosphere of nitrogen. Additional sodium methoxide in methanol (25% solution, 3 ml) was added and the reaction was stirred at 60° C. for a further 16 hours. An additional portion of sodium methoxide in methanol (25% solution, 5 ml) was added and the reaction was stirred at 90° C. for a further 7 hours. The solvent was removed on the rotary evaporator and the crude product was partitioned between EtOAc (75 ml) and saturated ammonium chloride solution (75 ml). The organic layer was washed with brine (75 ml). The solvent was removed on the rotary evaporator to yield the title compound as a pale orange foam (6 g).

후처리

  1. temperatureThe solution was heated
  2. stirringthe reaction was stirred at 90° C. for a further 7 hours
  3. customThe solvent was removed on the rotary evaporator
  4. customthe crude product was partitioned between EtOAc (75 ml) and saturated ammonium chloride solution (75 ml)
  5. washThe organic layer was washed with brine (75 ml)
  6. customThe solvent was removed on the rotary evaporator

출처 및 근거

ORD 기록
ord-99cfe944c94841f5972d09ff433c108c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346806B2

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