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

HRID 1511821Notes

Reaction equation

HRID 1511821 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fcaa68700e01447b9ff11752a9251042
Source dataset
uspto-grants-2012_07
Patent number
US08217042B2

Reaction notes

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