Cesium carbonate → N4-Isopropyl-N2-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidine-2,4-diamine

HRID 59152

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[C:4]([CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[C:32]([CH3:34])[N:31]=[N:30][CH:29]=1)[NH2:24].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:9]([NH:8][C:6]1[CH:5]=[C:4]([CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:3]=[C:2]([NH:24][C:23]2[CH:25]=[CH:26][C:27]([C:28]3[CH:33]=[C:32]([CH3:34])[N:31]=[N:30][CH:29]=3)=[C:21]([O:20][CH3:19])[CH:22]=2)[N:7]=1)([CH3:11])[CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 2-chloro-N-isopropyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (41 mg, 0.14 mmol), 3-methoxy-4-(6-methylpyridazin-4-yl)aniline (31 mg, 0.14 mmol), cesium carbonate (94 mg, 0.29 mmol), palladium(II) acetate (5 mg, 0.02 mmol) and 2-(dicyclohexyl-phosphino)biphenyl (8 mg, 0.02 mmol) in dioxane (2 mL) was heated under argon at 120° C. for 90 minutes in a microwave reactor. The mixture was filtered through a short silica gel plug which was washed with 10% solution of methanol in ethyl acetate. The eluate was concentrated in vacuum and the residue was purified by preparative HPLC to give the title compound 32 mg (48%).

Aufarbeitung

filtrationThe mixture was filtered through a short silica gel plug which
washwas washed with 10% solution of methanol in ethyl acetate
concentrationThe eluate was concentrated in vacuum
customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-3d4291e07d3442a8aa6d07ea9fd6ff84
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09439904B2

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