1,2-Dimethoxyethane → 4-Chloro-6-(2-Methoxyphenyl)pyrimidin-2-Amine

HRID 1890994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890994
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(COC)OC.C([O-])(O)=O.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH3:10])[N:5]=[C:4]([NH2:9])[N:3]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 655222-Amino-4,6-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acid

Produkt 1

HCID 468615524-Chloro-6-(2-Methoxyphenyl)pyrimidin-2-AmineAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4,6-dichloropyrimidin-2-ylamine (1.0 g, 6.13 mmol) and 2-methoxyphenylboronic acid (0.775 g, 5.1 mmol) were added to a solution of dimethoxyethane (20 mL) and water (3 mL), followed by the addition of NaHCO3 (1.03 g, 12.26 mmol) and (PPh3)2PdCl2 (0.2 g) to this and the reaction mixture was allowed to reflux for 4 h, and then the solvent removed under reduced pressure. The residue was taken up in ethyl acetate (50 mL), and the resulting solution washed with water, dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chropatography on silica gel (eluent CH2Cl2) and recrystallized from hexanes yielding 4-chloro-6-(2-methoxyphenyl)-pyrimidin-2-ylamine (0.76 g; 63%) as light yellow powder.

Aufarbeitung

  1. temperatureto reflux for 4 h
  2. customthe solvent removed under reduced pressure
  3. washthe resulting solution washed with water
  4. dry with materialdried over anhydrous K2CO3
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by flash chropatography on silica gel (eluent CH2Cl2)
  8. customrecrystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-864ed99ea41147b59b698855c56532a0
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507498B2

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