Potassium Carbonate → HCID 46838739, compound

HRID 1950790Notes

Reaction equation

HRID 1950790 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.C(OC(N[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=O)(C)(C)C.[C:33](=O)([O-])[O-:34].[K+].[K+]>O1CCOCC1.O.[Pd]>[CH3:33][O:34][C:24]1[CH:25]=[CH:26][C:27]([C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 46838739HCID 46838739, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 20 mL reaction vessel was charged with ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (1.00 g, 4.06 mmol), 4-(tert-butoxycarbonylamino)phenylboronic acid (1.00 g, 4.22 mmol), and tetrakis(triphenyl)phosphine)palladium(0) (0.17 g, 0.15 mmol) in 10 mL dioxane. The reaction mixture was purged with N2 for 25 minutes with stirring. To the mixture was added potassium carbonate (1.17 g, 8.44 mmol) in 4 mL H2O. The biphasic mixture was purged with N2 for 10 minutes. The mixture was stirred at 90° C. for 14 hours. The mixture was diluted with EtOAc, and washed with H2O. The separated organic layer was dried over Na2SO4. The solvents were removed by a rotavapor yielding brown oily residue. The residue was purified by silica gel chromatography using a gradient 0-5% MeOH in dichloromethane providing white solid (1.12 g, 68%). MS m/z: 319 (M+1)+.

Workup

  1. customA 20 mL reaction vessel
  2. customThe reaction mixture was purged with N2 for 25 minutes
  3. customThe biphasic mixture was purged with N2 for 10 minutes
  4. stirringThe mixture was stirred at 90° C. for 14 hours
  5. additionThe mixture was diluted with EtOAc
  6. washwashed with H2O
  7. dry with materialThe separated organic layer was dried over Na2SO4
  8. customThe solvents were removed by a rotavapor
  9. customyielding brown oily residue
  10. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a4ac5eec95c8451abbeddc1d8c6fae38
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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