Ethanol → 5-Bromo2-(6-hexyloxypyridin-3-yl)pyrimidine

HRID 376754Notes

Reaction equation

HRID 376754 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].Br[C:27]1[N:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=1>O.C1(C)C=CC=CC=1.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>[Br:33][C:30]1[CH:29]=[N:28][C:27]([C:11]2[CH:10]=[N:9][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:13][CH:12]=2)=[N:32][CH:31]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 109555882,5-DibromopyrimidineHCID 221125716-Hexyloxypyridine-3-boronic acid

Product 1

HCID 109697305-Bromo2-(6-hexyloxypyridin-3-yl)pyrimidineYield 40%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

233 mmol of 2-hexyloxypyridine-5-boronic acid, 300 ml of ethanol, a solution of 466 mmol of sodium carbonate in 150 ml of water and 2.3 mmol of tetrakis(triphenylphosphine)palladium(0) are added to a solution of 233 mmol of 2,5-dibromopyrimidine in 600 ml of toluene. The mixture is heated at the boil until the reaction is complete. The organic phase is separated off, the aqueous phase is extracted with dichloromethane, and the combined organic extracts are dried using sodium sulfate. After the solvent has been removed in vacuo, the crude product is separated off by column chromatography on silica gel 60 using dichloromethane as eluent and is recrystallized from n-heptane, giving 31 g (40%) of a colorless solid. m.p. 103-106° C.

Workup

  1. temperatureThe mixture is heated at the boil until the reaction
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. customthe combined organic extracts are dried
  5. customAfter the solvent has been removed in vacuo
  6. customthe crude product is separated off by column chromatography on silica gel 60 using dichloromethane as eluent
  7. customis recrystallized from n-heptane

Sources & evidence

ORD record
ord-c848971855c147439c3283f028e7007d
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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