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Chloroacetaldehyde → 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

HRID 1852951
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1852951
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=2)[N:5]=[C:4]([NH2:21])[CH:3]=1.P([O-])([O-])([O-])=O.[C:27]([O-])(=O)[CH3:28].[Na+].ClCC=O>C(O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[CH:12]=2)[N:5]2[CH:27]=[CH:28][N:21]=[C:4]2[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 33Chloroacetaldehyde2×HCID 1061PhosphateHCID 517045Sodium Acetate2×HCID 866852946-chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrimidin-4-amine

Produkt 1

HCID 866852957-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 6-chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrimidin-4-amine (2.750 g, 8.439 mmol) in 60 mL of 1:1 absolute ethanol: pH=7 phosphate buffer were added sodium acetate (1.385 g, 16.88 mmol) and 2-chloroacetaldehyde (1.905 mL, 14.77 mmol) and the reaction mixture was then fitted with a condenser and heated to 95° C. overnight. The reaction was not complete so sodium acetate (1.385 g, 16.88 mmol) and 2-chloroacetaldehyde (1.905 mL, 14.77 mmol) were added and the reaction mixture was heated to 95° C. for four hours. After this time the reaction was allowed to cool to ambient temperature and was then diluted with aqueous saturated sodium bicarbonate (50 mL) and extracted with ethyl acetate. The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography eluting with 30-45% ethyl acetate in hexanes (1 L) to afford the title compound (1.16 g, 3.315 mmol, 39.29% yield). MS (apci) m/z=350.1 (M+H).

Aufarbeitung

  1. customthe reaction mixture was then fitted with a condenser
  2. additionwere added
  3. temperaturethe reaction mixture was heated to 95° C. for four hours
  4. temperatureto cool to ambient temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with 30-45% ethyl acetate in hexanes (1 L)

Quellen und Nachweise

ORD-Eintrag
ord-67d63515ab9b45899887d6269679104e
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962596B2

Notizen zur Reaktion

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