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Chlorosuccinimide → 2-Amino-4-(1,2-dimethylimidazol-5-yl)-5-chloropyrimidine

HRID 1064347
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1064347
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[N:10][CH:9]=2)[C:5]([Cl:15])=[CH:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 222735092-Amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine

Produkt 1

HCID 222735602-Amino-4-(1,2-dimethylimidazol-5-yl)-5-chloropyrimidineAusbeute 233 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-Amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Method 26; 378 mg, 2 mmol) and N-chlorosuccimide (267 mg, 2 mmol) were dissolved in glacial acetic acid (7 ml) under an atmosphere of nitrogen. The reaction mixture was heated at 65° C. for 18 hours when further N-chlorosuccinimide (89 mg, 0.66 mmol) was added and the reaction heated at 65° C. for an additional 2 hours. The volatiles were removed by evaporation and the residue dissolved in water (10 ml). The solution was adjusted to pH 11-12 by addition of 40% aqueous sodium hydroxide solution. The precipitated solid was collected by filtration and washed sparingly with water, dried under vacuum at 60° C. to give the title compound (344 mg, 77%) as a yellow solid. NMR 2.35 (s, 3H, 3.75 (s, 3H), 4.83 (s, 2H), 7.53 (s, 1H), 8.27 (s, 1H); m/z 224.

Aufarbeitung

  1. additionwas added
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue dissolved in water (10 ml)
  4. additionThe solution was adjusted to pH 11-12 by addition of 40% aqueous sodium hydroxide solution
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed sparingly with water
  7. customdried under vacuum at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-acab7ec0e0684739985ff5a03ff4bc82
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06969714B2

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