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Pyridine → 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid

HRID 2296469
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2296469
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:24]([O:26]C)=[O:25].[I-].[Li+].N1C=CC=CC=1>O>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:24]([OH:26])=[O:25]
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Komponenten

5

Edukt 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 13060555methyl 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate

Produkt 1

HCID 130605594-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acidAusbeute 22,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of methyl 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (3.2 g), anhydrous lithium iodide (8.0 g) and dry pyridine (32 ml) was stirred at 120° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure to give a residue, which was dissolved in water. Insoluble materials were removed by filtration. The aqueous layer was adjusted to pH 1-2 with conc. hydrochloric acid to give crystals, which were separated by filtration and dried. The crude crystals were washed with methanol three times and recrystallized from acetonitrile to give 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (0.7 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue, which
  3. customInsoluble materials were removed by filtration
  4. customto give crystals, which
  5. customwere separated by filtration
  6. customdried
  7. washThe crude crystals were washed with methanol three times
  8. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a8fc7249e4ff471bb23f11f285d0b40d
Quelldatensatz
uspto-grants-1984_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04429126

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