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Trifluoroacetic anhydride → HCID 59380350, Verbindung

HRID 2353314
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2353314
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([NH:13][CH2:14][CH:15](OC)OC)[N:5]=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[N:3]=1.FC(F)(F)C(O)=O.ClCCl.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[N:5]2[CH:15]=[CH:14][N:13]=[C:6]2[C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 57542080HCID 57542080, Verbindung

Produkt 1

HCID 59380350HCID 59380350, VerbindungAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Methyl [4-chloro-6-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (100 mg, 0.19 mmol) was treated with 50% trifluoroacetic acid/dichloromethane (5 mL) at room temperature overnight. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with aq NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (5 mL). To the solution was added trifluoroacetic anhydride (0.053 mL, 0.38 mmol). The mixture was stirred at room temperature for 3 hours. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with aq NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC (silica gel, chloroform:ethanol, 19/1) to give methyl [7-chloro-5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (22 mg, 25%) as a colorless film.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with aq NaHCO3 and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in dichloromethane (5 mL)
  7. extractionextracted with dichloromethane
  8. washThe extracts were washed with aq NaHCO3 and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified by preparative TLC (silica gel, chloroform:ethanol, 19/1)

Quellen und Nachweise

ORD-Eintrag
ord-26148577e27e4eafb0f3f6d5ec572c6a
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07750014B2

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