Sodium Hydroxide → 5-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1481249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481249
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([NH2:17])=[CH:4][N:3]=1.[N:18]([O-])=O.[Na+].[OH-].[Na+]>Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:17]=[N:18][N:8]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 897194042-Chloro-N4-(4-methoxyphenyl)pyrimidine-4,5-diamine

Produkt 1

HCID 897179715-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 1.51 g (6.02 mmol) 2-chloro-N4-(4-methoxy-phenyl)-pyrimidine-4,5-diamine in 75 ml 37% aqueous hydrochloric acid is treated with 852 mg (12.4 mmol) sodium nitrite. The mixture is stirred for 16 hours at room temperature. Aqueous sodium hydroxide is added to the reaction mixture to reach a neutral pH-value. Then the mixture is extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated giving 5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine as brown solid; HPLC/MS (A): 1.89 min, [M+H] 262;

Aufarbeitung

  1. extractionThen the mixture is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6f87b058189e4b6ea2712e96c68e8563
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409914B2

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