Water → (6-Chloro-2-methoxymethyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine

HRID 2110766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110766
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH2:9][O:10][CH3:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH2:20][CH2:21][NH2:22].C(=O)(O)[O-].[Na+].O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([CH2:9][O:10][CH3:11])[N:3]=[C:2]([NH:22][CH2:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])[CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1429382,4-DichlorophenethylamineHCID 516892Sodium BicarbonateHCID 534381214,6-Dichloro-2-(methoxymethyl)pyrimidine

Produkt 1

HCID 86615707(6-Chloro-2-methoxymethyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amineAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4,6-dichloro-2-methoxymethyl-pyrimidine (250 mg, 1.3 mmol), 2-(2,4-dichloro-phenyl)-ethylamine (196 μL, 1.3 mmol), and sodium bicarbonate (218 mg, 2.6 mmol) in EtOH (5 mL) is heated at 80° C. for three hours and poured into water (20 mL) and extracted thrice with EtOAc (30 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and evaporated. The residue is subjected to chromatography on silica gel eluting with 30% ethyl acetate:heptane to afford (6-chloro-2-methoxymethyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (200 mg, 44%) as a solid.

Aufarbeitung

  1. extractionextracted thrice with EtOAc (30 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6310b4a417094ceaa0b9215e43abf649
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517889B2

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