Cesium carbonate → HCID 69070693, Verbindung

HRID 216192

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine [250 mg, 0.74 mmol, Intermediate (31)], 3-hydroxy-benzoic acid ethyl ester (0.18 g, 1.1 mmol), and Cs2CO3 (0.48 g, 1.48 mmol) in DMF (4 mL) is heated to 90° C. for 15 h. The mixture is diluted with water, and extracted with EtOAc. The extracts are washed (water), dried (MgSO4), filtered, concentrated, and chromatographed (silica gel, 30% EtOAc in Heptane) to afford 3-{6-[2-(3,4-dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yloxy}-benzoic acid ethyl ester [0.29 g, 83%, Intermediate (71)]. LCMS: RT=3.7 minutes, MS: 470 (M+H).

Aufarbeitung

extractionextracted with EtOAc
washThe extracts are washed (water)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customchromatographed (silica gel, 30% EtOAc in Heptane)

Quellen und Nachweise

ORD-Eintrag: ord-596feaa9dcfd49b8b8810981e291526a
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193183B2

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