Sodium Carbonate → 5-[6-(2-Fluoro-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-pyridin-2-ylamine

HRID 1512132

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:3]=1.[F:21][C:22]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[CH:24][N:23]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[F:21][C:22]1[C:27]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=[C:4]([C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)[CH:3]=2)=[CH:26][CH:25]=[CH:24][N:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 5-(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)pyridin-2-ylamine, prepared as in Example 2, (252 mg, 0.87 mmol) and 2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (183 mg, 1.30 mmol) in DME (4 mL) was added an aqueous solution of Na2CO3 (2 M, 1 mL), followed by dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane (71 mg, 0.087 mmol). The mixture was heated in a microwave for 20 min at 120° C. The aqueous phase was separated from DME, and extracted with EtOAc. The combined organic phases were washed with brine, dried, filtered, and concentrated to give crude desired product which was carried on to the next step without further purification. LC/MS (m/z): 353.3 (MH+), 1.84 minutes.

Aufarbeitung

customThe aqueous phase was separated from DME
extractionextracted with EtOAc
washThe combined organic phases were washed with brine
customdried
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-32fba1c7ca114f948f3e66796c5ed070
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08217035B2

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