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Methanol → 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1878038
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1878038
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7](=[O:21])[N:6]([CH3:22])[C:5]2([CH2:27][N+:28]([O-])=O)[C:23]([F:26])([F:25])[F:24].CO.O.[Cl-].[NH4+]>C1COCC1.[Fe]>[NH2:28][CH2:27][C:5]1([C:23]([F:25])([F:26])[F:24])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:7](=[O:21])[N:6]1[CH3:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 684891426-bromo-1-(4-methoxybenzyl)-3-methyl-4-(nitromethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Produkt 1

HCID 684894644-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 23925IronKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

6-Bromo-1-(4-methoxybenzyl)-3-methyl-4-(nitromethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (217.3 mg, 0.445 mmol) was dissolved in THF (0.9 mL), methanol (0.9 mL) and water (0.5 mL), and iron (497 mg, 8.9 mmol) and ammonium chloride (476 mg, 8.9 mmol) were sequentially added to the reaction solution at room temperature. The reaction solution was stirred at 90° C. for 2.5 hours and then cooled to room temperature and insoluble substances were removed by Celite filtration. After the solvent was evaporated under reduced pressure, to the residue, chloroform and saturated sodium hydrogen carbonate were added, and the mixture was stirred at room temperature. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/4), whereby the objective 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (148.3 mg, 72.7%) was obtained as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custominsoluble substances were removed by Celite filtration
  3. customAfter the solvent was evaporated under reduced pressure, to the residue, chloroform and saturated sodium hydrogen carbonate
  4. additionwere added
  5. stirringthe mixture was stirred at room temperature
  6. customThe organic layer was separated
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customAfter the drying agent was removed by filtration
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/4), whereby the objective 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (148.3 mg, 72.7%)
  12. customwas obtained as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-58af03f8794843f5aa53ddeaab622340
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08314094B2

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