Ethanol → HCID 20095037, compound

HRID 1770188Notes

Reaction equation

HRID 1770188 reaction equation
[CH2:1]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11](B(O)O)[CH:12]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].Br[C:19]1[CH:20]=[N:21][C:22](Cl)=[N:23][CH:24]=1.[CH2:26](O)[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:22]3[N:21]=[CH:20][C:19]([C:11]4[CH:12]=[C:13]5[C:8](=[CH:9][CH:10]=4)[CH2:7][CH:6]([CH2:1][CH2:2][CH2:3][CH2:26][CH3:27])[CH2:14]5)=[CH:24][N:23]=3)[CH:12]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 20095041HCID 20095041, compound

Product 1

HCID 20095037HCID 20095037, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

1.0 g (4.3 mM) of 2-pentylindan-5-boronic acid, 0.42 g (2.16 mM) of 5-bromo-2-chloropyrimidine, 4 ml of ethanol, 6 ml of benzene, 6 ml of 2M-sodium carbonate aqueous solution and 0.18 g of tetrakis (triphenylphosphine)palladium (O) were mixed and heat-refluxed for 2 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.63 g (1.40 mM) of 2,5-bis(2-pentylindan-5-yl)pyrimidine (Yield: 65%). ##STR328##

Workup

  1. temperatureheat-refluxed for 2 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. custompurified by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-9b042e39cb024d04bbf6a4b15b7c461d
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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