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Ammonium Hydroxide → 4-(4-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-amine

HRID 535747
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 535747
[Br:1][C:2]1[N:3]=[C:4]([CH:22]2[CH2:24][CH2:23]2)[N:5]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9](Cl)[N:8]=1.[NH4+:25].[OH-]>O1CCOCC1.O>[Br:1][C:2]1[N:3]=[C:4]([CH:22]2[CH2:24][CH2:23]2)[N:5]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:25])[N:8]=1
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Komponenten

5

Edukt 2

HCID 14923Ammonium HydroxideHCID 866514084-(4-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy) methyl)-1H-imidazol-5-yl)-2-chloropyrimidine

Produkt 1

HCID 698129254-(4-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-amineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

4-(4-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-2-chloropyrimidine (1 g, 2.4 mmol) was combined with aqueous 28% NH4OH solution (8 mL) in 1,4-dioxane (8 mL) and the resulting mixture was split evenly between two reaction vials. Each was irradiated in a microwave reactor for 40 minutes at 130° C. TLC analysis indicated complete reaction. The combined reactions were then diluted with water (100 mL) followed by extraction with EtOAc (100 mL). The EtOAc layer was washed with brine then dried (Na2SO4), and concentrated. Purification of the resulting residue by flash chromatography on silica gel using an EtOAc-hexanes gradient (0 to 60%) provided 0.87 g of (2.1 mmol, 91%) of 4-(4-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-amine as a white solid: LCMS (m/z): 410.0 (MH+), tR=0.81 minute.

Aufarbeitung

  1. customthe resulting mixture was split evenly between two reaction vials
  2. customEach was irradiated in a microwave reactor for 40 minutes at 130° C
  3. customreaction
  4. extractionfollowed by extraction with EtOAc (100 mL)
  5. washThe EtOAc layer was washed with brine
  6. dry with materialthen dried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification of the resulting residue by flash chromatography on silica gel using an EtOAc-hexanes gradient (0 to 60%)

Quellen und Nachweise

ORD-Eintrag
ord-6ebb9dc3b1104f3eb07360e377f9ffea
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08859548B2

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