4-(4-Bromobenzyl)morpholine → 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-N-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine

HRID 56

Reaktionsgleichung

Reaktionsgleichung von HRID 56
Brc1ccc(CN2CCOCC2)cc1.Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCC(C)(C)[O-].CCCCOC(C)=O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3)ncc2F)n1C1CCOCC1

Komponenten

7

Edukt 2

HCID 7835034-(4-Bromobenzyl)morpholineHCID 166654985-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

Produkt 1

HCID 166652515-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-N-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amineAusbeute 0 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733478Sodium 2-methylbutan-2-olateReagenzHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylKatalysatorHCID 31272Butyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Tris(dibenzylideneacetone)dipalladium(0) (4.5 mg, 4.91 µmol) and 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (4.38 mg, 9.20 µmol) were dissolved in butyl acetate (1.8 mL) in a 10 mL Schlenk tube and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (51 mg, 0.18 mmol), 4-(4-bromobenzyl)morpholine (49.5 mg, 0.19 mmol) and Sodium tert-pentoxide (32.4 mg, 0.29 mmol) were added. It was degassed again and stirred at 100 °C under argon. The reaction was followed by HPLC. After 4.5 h no conversion was observed. Hence the whole reaction mixture was discarded.

Quellen und Nachweise

ORD-Eintrag
ord-dd820c31fef4456fb96fcbe0cfbfed80
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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