Hydrochloric Acid → 1-Ethyl-3-(3-phenylethynylpyrido[2,3-b]pyrazin-6-yl)urea

HRID 1511818Notes

Reaction equation

HRID 1511818 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C)C=O.ClCCl.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:16]([NH:15][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:5]2[C:6]([N:8]=1)=[N:7][C:2]([C:32]#[C:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:3][N:4]=2)=[O:14])[CH3:17]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 588817911-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea

Product 1

HCID 166665761-Ethyl-3-(3-phenylethynylpyrido[2,3-b]pyrazin-6-yl)urea

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

98.1 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.39 mmol), 10.1 mg copper(I) iodide (0.05 mmol) and 193 μl of triethylamine (1.38 mmol) were initially charged in 2 ml of anhydrous dimethylformamide under nitrogen as a protective gas. Subsequently, 29.1 mg of dichlorobis(triphenylphosphine)palladium(II) (0.04 mmol) and 54 μl of phenylacetylene (0.49 mmol) were added, and the mixture was stirred at room temperature for 16 h. For workup, the mixture was diluted with dichloromethane and added to dilute hydrochloric acid. The precipitated solid was filtered off with suction, and the organic phase was washed with dilute hydrochloric acid and distilled water. After phase separation, the organic solvent was removed under reduced pressure. The further purification was effected by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washthe organic phase was washed with dilute hydrochloric acid
  3. distillationdistilled water
  4. customAfter phase separation
  5. customthe organic solvent was removed under reduced pressure
  6. customThe further purification
  7. customThis gave a yellow solid

Sources & evidence

ORD record
ord-fc021ba4f70941f59ebcc2a51c1df7dd
Source dataset
uspto-grants-2012_07
Patent number
US08217042B2

Reaction notes

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