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

HRID 1095021

Reaktionsgleichung

Reaktionsgleichung von HRID 1095021
[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>[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

6

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 1

HCID 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)j (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-d0aa79fbcbb84cd4ae226e9a8cc7e2cf
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133900B2

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