Toluene → HCID 53830912, compound

HRID 1457499Notes

Reaction equation

HRID 1457499 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[N:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:23][N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[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.C(O)C>[CH2:27]([C:24]1[CH:23]=[N:22][C:21]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:12][CH:13]=2)=[N:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11543402Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-HCID 220990832-Chloro-5-decylpyrimidine

Product 1

HCID 53830912HCID 53830912, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1.27 g (4.96 mmol) of 4-(2-benzyloxyethyl) phenylboronic acid, 1.26 g (4.96 mmol) of 2-chloro-5-decylpyrimidine, 0.19 g of tetrakis (triphenylphosphine) palladium, 8 ml of 2M sodium carbonate, 8 ml of toluene and 4 ml of ethanol were, under presence of nitrogen, heated at 80° C. for 3 hours. After the reactions had been completed, extraction with toluene was performed and the extracted solution was dried with anhydrous sodium sulfate. The solvent was removed by filtration and refining was performed by recrystallization (toluene/methanol) so that 1.65 g of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether was obtained (yield 77%).

Workup

  1. extractionextraction with toluene
  2. dry with materialthe extracted solution was dried with anhydrous sodium sulfate
  3. customThe solvent was removed by filtration and refining
  4. customwas performed by recrystallization (toluene/methanol) so that 1.65 g of 2-{4-(5-decylpyrimidine-2-yl) phenyl}ethylbenzylether
  5. customwas obtained (yield 77%)

Sources & evidence

ORD record
ord-880d47d1514440a8802feee75e156a9d
Source dataset
uspto-grants-1998_12
Patent number
US05849217

Reaction notes

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