Cesium carbonate → 2-(2,6-Dichlorophenyl)-N-(2,6-dimethylpyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine

HRID 2366174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366174
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([CH3:27])[N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:26][C:24]3[CH:23]=[C:22]([CH3:27])[N:21]=[C:20]([CH3:19])[N:25]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 862804124-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine

Produkt 1

HCID 569531082-(2,6-Dichlorophenyl)-N-(2,6-dimethylpyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 2,6-dimethylpyrimidin-4-amine (0.027 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos ((0.017 g, 0.034 mmol) and Cs2CO3 (0.111 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a white solid (14 mg, 21% yield). 1H NMR (500 MHz, CH3OH-d4): δ 8.44 (d, J=5.5 Hz, 1H), 7.71 (d, J=5.5 Hz, 1H), 7.56-7.51 (m, 4H), 7.31 (s, 1H), 2.44 (s, 3H), 2.35 (s, 3H). LCMS (Method A): RT=5.75 min, m/z: 402.0 [M+H+].

Aufarbeitung

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customwas removed via filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified with reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

Quellen und Nachweise

ORD-Eintrag
ord-8116a08d96694e339aeac497e94e3e29
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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