Cesium carbonate → 2-chloro-N-(2,4-dichloro-5-methoxyphenyl)-5-methylpyrimidin-4-amine

HRID 1097079

Reaktionsgleichung

Reaktionsgleichung von HRID 1097079
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.Br[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([Cl:19])=[CH:13][C:12]=1[Cl:20].C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>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:1][C:2]1[N:7]=[C:6]([NH:8][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([Cl:19])=[CH:13][C:12]=2[Cl:20])[C:5]([CH3:9])=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 196077211-Bromo-2,4-dichloro-5-methoxybenzene

Produkt 1

HCID 575164812-chloro-N-(2,4-dichloro-5-methoxyphenyl)-5-methylpyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To a solution of 2-chloro-5-methylpyrimidin-4-amine (44.8 mg, 0.31 mmol) in 1,4-dioxane (20 mL) was added 1-bromo-2,4-dichloro-5-methoxybenzene (96 mg, 0.37 mmol), Cs2CO3 (408 mg, 1.25 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (Xant Phos, 70 mg, 0.12 mmol). The mixture was heated under reflux for 4 h under Ar. The solid was filtered off and the filtrate washed with brine (1×100 mL). The organic solution was separated and dried (Na2SO4). The solvent was removed in vacuo. The crude product was used for next reaction without purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h under Ar
  3. filtrationThe solid was filtered off
  4. washthe filtrate washed with brine (1×100 mL)
  5. customThe organic solution was separated
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customThe crude product was used for next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-c3f8cc4f336b426893ca41899a6ba0d9
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138199B2

Verknüpfte Notizen

Wird geladen…