Cesium carbonate → 4-(((3,3-Difluorocyclobutyl)methoxy)methyl)-6-(1-ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)pyrimidin-2-amine

HRID 59082

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([CH2:8][O:9][CH2:10][CH:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)[CH:5]=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[N:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[C:31]1[CH:36]=[C:35]([CH3:37])[N:34]=[N:33][CH:32]=1)[NH2:27].C(=O)([O-])[O-].[Cs+].[Cs+].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:15][C:13]1([F:16])[CH2:14][CH:11]([CH2:10][O:9][CH2:8][C:6]2[CH:5]=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[N:3]=[C:2]([NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:31]4[CH:36]=[C:35]([CH3:37])[N:34]=[N:33][CH:32]=4)=[C:24]([O:23][CH3:22])[CH:25]=3)[N:7]=2)[CH2:12]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 2-chloro-4-(((3,3-difluorocyclobutyl)methoxy)methyl)-6-(1-ethoxyvinyl)pyrimidine (0.068 g, 0.21 mmol), 3-methoxy-4-(6-methylpyridazin-4-yl)aniline (0.046 g, 0.21 mmol), cesium carbonate (0.139 g, 0.43 mmol), palladium (II) acetate (7 mg, 0.03 mmol) and (2-biphenylyl)dicyclohexylphosphine (0.011 g, 0.03 mmol) in dioxane (2 mL) was heated under argon at 120° C. for 90 min in microwave reactor. The mixture was filtered through a short silica plug and was eluted with 10% MeOH in EtOAc. The solvents were evaporated to give the title compound (0.109 g, quant).

Aufarbeitung

filtrationThe mixture was filtered through a short silica plug
washwas eluted with 10% MeOH in EtOAc
customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag: ord-2bc56a693ef549deb08355a270cdc4fc
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09439904B2

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