1,2,3,4-Tetrahydroquinoline → 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine

HRID 75

Reaktionsgleichung

Reaktionsgleichung von HRID 75
Clc1ccnc(Cl)n1.c1ccc2c(c1)CCCN2>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Clc1nccc(N2CCCc3ccccc32)n1

Komponenten

7

Edukt 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 775312,4-Dichloropyrimidine

Produkt 1

HCID 227319232-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidineAusbeute 7,28 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2,4-dichloropyrimidine (200 mg, 1.34 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (78 mg, 0.13 mmol), Tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and Cesium carbonate (656 mg, 2.01 mmol) was added to a microwave vial. toluene (2 mL) was added. 1,2,3,4-tetrahydroquinoline (179 mg, 1.34 mmol) was added. Heated to 120ºC in microwave oven for 90min. Crude filtered through celite and then added to prepHPLC. 30-70% acetonitrile in water. Pure fractions pooled and then freezedried over night. Yielded 1-(2-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline (24.00 mg, 7.28 %)

Quellen und Nachweise

ORD-Eintrag
ord-4dd72fee5c294abbb8cdefc25f205782
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
Quelle ansehen

Verknüpfte Notizen

Wird geladen…