5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine → 5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

HRID 16

Reaktionsgleichung

Reaktionsgleichung von HRID 16
Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>CCC(C)(C)[O-].Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.[Na+].[Pd]>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1

Komponenten

7

Edukt 2

HCID 166654985-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amineHCID 534178184-(4-Bromo-3-fluorobenzyl)morpholine

Produkt 1

HCID 497820135-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733478Sodium 2-methylbutan-2-olateReagenzHCID 23938PalladiumKatalysatorHCID 80271Tri-o-tolylphosphineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Tri-o-tolylphosphine (49.4 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 88 % conversion was achieved. The reaction was stopped and the mixture was discarded.

Quellen und Nachweise

ORD-Eintrag
ord-b9ea1ddb99074c47af3b567d6c34306c
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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