Phosphorus oxychloride → 2-Chloro-4-neopentylamino-6-nitroquinazoline

HRID 1250563

Reaktionsgleichung

Reaktionsgleichung von HRID 1250563
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.[CH2:21]([NH2:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>O>[Cl:18][C:9]1[N:8]=[C:7]([NH:26][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 79882NeopentylamineHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Produkt 1

HCID 183263792-Chloro-4-neopentylamino-6-nitroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 367 mg (1.77 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 15.13 g (98.70 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 309 mg (3.54 mmol) of neopentylamine under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, and crystals thus precipitated were filtered out to obtain 2-chloro-4-neopentylamino-6-nitroquinazoline. The compound was dissolved in 2 ml of DMF, and after 1.52 g (26.65 mmol) of allylamine was added to the resulting solution, the mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 210 mg (yield: 37.6%) of the title compound.

Aufarbeitung

  1. customreaction in the same manner as in Example 10
  2. customthus precipitated
  3. filtrationwere filtered out

Quellen und Nachweise

ORD-Eintrag
ord-0e13dbc75b8543418dff0d8b97e2279b
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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