Ammonium Chloride → 1-(3-Benzylpyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

HRID 1511821노트

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HRID 1511821 반응식
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[N:16]=[C:15]2[N:17]=[C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:14]2=[N:13][CH:12]=1.[Cl-].[NH4+]>C1COCC1.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:11]1[N:16]=[C:15]2[N:17]=[C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:14]2=[N:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 588817911-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylureaHCID 178419772HCID 178419772, 화합물

생성물 1

HCID 166673101-(3-Benzylpyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

2.4 ml of a 0.5 M solution of benzylzinc bromide (1.20 mmol) in THF and 24.7 mg of tetrakis(triphenylphosphine)palladium(0) (0.02 mmol) were initially charged in 1 ml of dioxane under nitrogen. Subsequently, 102.4 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.41 mmol) and 1 ml of dioxane were added in portions. The mixture was then heated to 100° C. After 7 h, the reaction mixture was allowed to cool and then saturated ammonium chloride solution was added. The aqueous phase was extracted repeatedly with dichloromethane and the collected organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and freed from the solvent under reduced pressure. Column chromatography purification on silica gel (dichloromethane/methanol eluent) afforded a yellow solid.

후처리

  1. temperatureto cool
  2. extractionThe aqueous phase was extracted repeatedly with dichloromethane
  3. washthe collected organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customColumn chromatography purification on silica gel (dichloromethane/methanol eluent)
  6. customafforded a yellow solid

출처 및 근거

ORD 기록
ord-fcaa68700e01447b9ff11752a9251042
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217042B2

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