Ethyl Acetate → HCID 58497003, compound

HRID 1697273Notes

Reaction equation

HRID 1697273 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14](B(O)O)[CH:13]=[CH:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.CO.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.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:15]=2)[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 58496903HCID 58496903, compound

Product 1

HCID 58497003HCID 58497003, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 400 mg 6-tert.-butoxycarbonylamino-naphthalene-2-boronic acid, 258 mg 2-bromo-pyrimidine, 100 mg tetrakis(triphenylphosphine)palladium and 4 ml 1 M sodium carbonate solution in 15 ml dioxane and 5 ml of methanol is refluxed for four hours in an argon atmosphere. After cooling to ambient temperature the reaction mixture is divided between ethyl acetate and water. The organic phase is dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (75:25 to 50:50) as eluant.

Workup

  1. temperatureis refluxed for four hours in an argon atmosphere
  2. customThe organic phase is dried on magnesium sulphate
  3. customevaporated down
  4. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (75:25 to 50:50) as eluant

Sources & evidence

ORD record
ord-f2baa1aea34c4f92bc514704f6dff881
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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