Imidazole → 2-Imidazolyl-4,6-dichloropyrimidine

HRID 23186

Reaktionsgleichung

Reaktionsgleichung von HRID 23186
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:7]1[C:8]([Cl:14])=[N:9][C:10](Cl)=[N:11][CH:12]=1.C(N(CC)CC)C.[Cl-:22].[NH4+]>C1COCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:10]1[N:11]=[C:12]([Cl:22])[CH:7]=[C:8]([Cl:14])[N:9]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2372592,4,5-Trichloropyrimidine

Produkt 1

HCID 221700012-Imidazolyl-4,6-dichloropyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Imidazole (9.5 g, 140 mmol) was added in one portion to a solution of trichloropyrimidine (24.7 g, 135 mmol) and triethylamine (30 mL, 216 mmol) in THF (500 mL). After 16 hrs, the reaction mixture was poured into saturated, aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. The reaction mixture was filtered and all volatiles were removed under reduced pressure. 2-Imidazolyl-4,6-dichloropyrimidine (the compound of formula (VIIIa)) (9.61 g, 33%) was isolated by flash chromatography (20% ethyl acetate in hexane) as an off-white solid. 1H NMR: (CDCl3) δ 7.13 (s,1), 7.25 (s,1), 7.76 (s,1), 8.50 (s, 1).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe reaction mixture was filtered
  5. customall volatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5166686b963f4292b26369a10eef036a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849739B2

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