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

HRID 385546ノート

反応式

HRID 385546 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium Carbonate2 回HCID 780681,3-Dioxolane, 2-(bromomethyl)-2 回HCID 578153663-Methoxypyrido[2,3-b]pyrazin-6(5H)-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-32cfef15308e46778995f254ece1a251
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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