Toluene → HCID 59570657, compound

HRID 1961708Notes

Reaction equation

HRID 1961708 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]([C:31]2[CH:36]=[N:35][CH:34]=[C:33](Cl)[N:32]=2)[C:28](=[O:30])[OH:29])=[CH:23][CH:22]=1.[Cl-].[Li+].[C:40]1([CH3:46])[CH:45]=CC=C[CH:41]=1>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>[C:40]([O:29][C:28](=[O:30])[N:27]([C:24]1[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=1)[C:31]1[CH:36]=[N:35][CH:34]=[C:33]([C:6]2[N:7]=[CH:8][CH:9]=[CH:10][N:11]=2)[N:32]=1)([CH3:46])([CH3:45])[CH3:41]

Participants

6

Reactant 4

HCID 1140TolueneHCID 433294Lithium ChlorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 86647347HCID 86647347, compound

Product 1

HCID 59570657HCID 59570657, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

Bis(triphenylphosphine)palladium(II) dichloride (95 mg, 0.13 mmol) and 2-(tributylstannyl)-pyrimidine (493 mg, 1.34 mmol) were added to a degassed solution of (4-chloro-phenyl)-(6-chloro-pyrazin-2-yl)-carbamic acid tent-butyl ester (500 mg, 1.47 mmol) and lithium chloride (170 mg, 4.00 mmol) in toluene (5 mL) and the mixture was heated to reflux over night. The reaction was quenched with aqueous sodium hydrogen carbonate and brine. The aqueous phase was extracted with ethyl acetate (4×15 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulphate, filtrated and evaporated. The crude product was purified by column chromatography (ethyl acetate/heptane as eluent) to give (4-chloro-phenyl)-(6-pyrimidin-2-yl-pyrazin-2-yl)-carbamic acid tert-butyl ester (53 mg, 10%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux over night
  3. customThe reaction was quenched with aqueous sodium hydrogen carbonate and brine
  4. extractionThe aqueous phase was extracted with ethyl acetate (4×15 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltrated
  8. customevaporated
  9. customThe crude product was purified by column chromatography (ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-3e45182283f0438d8c9596a6f7377e58
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

Loading…