Ethanol → HCID 19386219, compound

HRID 2399197Notes

Reaction equation

HRID 2399197 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH2:9]([O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)[CH2:10][CH3:11].[C:22](=[O:25])([O-])[O-].[Na+].[Na+].[CH2:28](O)[CH3:29]>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.O>[CH2:9]([O:12][C:13]1[CH:14]=[C:15]([C:2]2[N:7]=[CH:6][C:5]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([O:25][CH2:22][CH2:28][CH3:29])[CH:18]=3)=[CH:4][N:3]=2)[CH:16]=[CH:17][CH:18]=1)[CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 3691230(3-Propoxyphenyl)boronic acidHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 19386219HCID 19386219, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.0 g (8.4 mmol) of 2,5-dibromopyrimidine, 4.54 g (25.2 mmol) of 3-propoxybenzeneboronic acid, 5.34 g (50.4 mmol) of sodium carbonate and 0.10 g (0.9 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 6 hours in 50 ml of toluene, 25 ml of ethanol and 25 ml of water. The reaction mixture is subsequently partitioned between water and ether, the organic phase is washed twice with sodium chloride solution, dried over sodium sulfate and evaporated, and the residue is purified by chromatography (silica gel/dichloromethane:ethyl acetate=98:2) and by recrystallization from n-hexane, giving 1.31 g of 2,5-bis(3-propoxyphenyl)pyrimidine. ##STR27## The compound has the phase sequence: X 81 I 31.6 X

Workup

  1. customThe reaction mixture is subsequently partitioned between water and ether
  2. washthe organic phase is washed twice with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customthe residue is purified by chromatography (silica gel/dichloromethane:ethyl acetate=98:2) and by recrystallization from n-hexane

Sources & evidence

ORD record
ord-c5b985ff1c5c4aa5a6cf1423796da915
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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