Water → 5-(1,3-dioxolan-2-ylmethyl)-3-methoxypyrido(2,3-b)pyrazin-6(5H)-one

HRID 1510666노트

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HRID 1510666 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][C:10](=[O:13])[CH:11]=[CH:12][C:6]2=[N:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1.O>CN(C)C=O.C(OCC)(=O)C>[O:23]1[CH2:24][CH2:25][O:26][CH:22]1[CH2:21][N:9]1[C:7]2=[N:8][C:3]([O:2][CH3:1])=[CH:4][N:5]=[C:6]2[CH:12]=[CH:11][C:10]1=[O:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium Carbonate2회HCID 780681,3-Dioxolane, 2-(bromomethyl)-2회HCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-one

생성물 1

HCID 578154155-(1,3-dioxolan-2-ylmethyl)-3-methoxypyrido(2,3-b)pyrazin-6(5H)-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a solution of 0.30 g of 3-methoxypyrido(2,3-b)pyrazin-6(5H)-one in 6 mL of N,N-dimethylformamide, 0.35 g of potassium carbonate was added, and the mixture was stirred at 65 to 75° C. for 10 minutes. Thereto was added 0.21 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 95 to 100° C. for 1 hour 30 minutes. Thereto were further added 0.05 mL of 2-bromomethyl-1,3-dioxolan and 120 mg of potassium carbonate, and the mixture was stirred at 95 to 100° C. for 2 hours 15 minutes. The reaction mixture was cooled to room temperature, and water and ethyl acetate were then added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=2:1 to obtain 0.13 g of 5-(1,3-dioxolan-2-ylmethyl)-3-methoxypyrido(2,3-b)pyrazin-6(5H)-one as a yellow solid.

후처리

  1. stirringthe mixture was stirred at 95 to 100° C. for 1 hour 30 minutes
  2. stirringthe mixture was stirred at 95 to 100° C. for 2 hours 15 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1786d711bbab46488ce9831188b330ea
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211908B2

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