Toluene → 2-{4-(5-Decyloxypyrimidine-2-yl) phenyl}ethylbenzylether

HRID 1457501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457501
[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]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[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>[CH2:28]([O: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)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11543402Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-HCID 220990812-Chloro-5-decyloxypyrimidine

Produkt 1

HCID 542578172-{4-(5-Decyloxypyrimidine-2-yl) phenyl}ethylbenzyletherAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

8.62 g (33.7 mmol) of 4-(2-benzyloxyethyl) phenyl boronic acid, 9.13 g (33.7 mmol) of 2-chloro-5-decyloxypyrimidine, 1.29 g of tetrakis (triphenylphosphine) palladium, 54 ml of 2M-sodium carbonate solution, 54 ml of toluene and 27 ml of ethanol were heated at 80° C. for 4 hours under presence of nitrogen. After reactions had been completed, extraction with toluene was performed. Then, the extracted solution was dried with anhydrous sodium sulfate. The solvent was removed by filtration, and then refining was performed by recrystallization (toluene/methanol) so that 9.30 g of 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethylbenzylether was obtained (yield 62%).

Aufarbeitung

  1. extractionextraction with toluene
  2. dry with materialThen, the extracted solution was dried with anhydrous sodium sulfate
  3. customThe solvent was removed by filtration
  4. customrefining was performed by recrystallization (toluene/methanol) so that 9.30 g of 2-{4-(5-decyloxypyrimidine-2-yl) phenyl}ethylbenzylether
  5. customwas obtained (yield 62%)

Quellen und Nachweise

ORD-Eintrag
ord-463f91c0f86e4db9b00dee669b36b17a
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849217

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