Cesium carbonate → {4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester

HRID 19507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19507
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:26]=[C:25]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[N:24]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:22][C:23]2[N:24]=[C:25]([C:37]3[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)[CH:26]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[N:28]=2)=[CH:8][C:7]=1[CH3:13]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 23549552Methyl 2-(4-hydroxy-2-methylphenoxy)acetateHCID 590076462-Bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine

Produkt 1

HCID 59007643{4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(4-Hydroxy-2-methyl-phenoxy)-acetic acid methyl ester 4 (0.13 g, 0.66 mmol) is dissolved in dry acetonitrile (3 mL). Cesium carbonate (0.40 g, 1.2 mmol) is added, followed by 32-bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine 24 from Step C above. The mixture is stirred under nitrogen at room temperature for 18 hours. The resulting suspension is filtered, the solids are washed with more acetonitrile, and the resulting clear solution is concentrated to yield crude {4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester 25 as an oil. MS calculated for C29H29N2O6 (M+H+) 500.19. found 500.1.

Aufarbeitung

  1. filtrationThe resulting suspension is filtered
  2. washthe solids are washed with more acetonitrile
  3. concentrationthe resulting clear solution is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f230f2b516d34ba7baca831b87570b8b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745445B2

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