Hydrochloric Acid → 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid

HRID 354895

Reaktionsgleichung

[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:25])[CH2:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:26]([O:28]C)=[O:27].[I-].[Li+].Cl>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:25])[CH2:18][CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:26]([OH:28])=[O:27]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of methyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (5.72 g) and anhydrous lithium iodide (14.3 g) in dry pyridine (59 ml) was stirred at 120° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure to give crystalline residue, which was suspended in water (100 ml). The suspension was adjusted to pH 1.7 with conc. hydrochloric acid to yield yellow crystals, which were separated by filtration, washed with water and dried. Recrystallization from N,N-dimethylformamide gave crystalline 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (4.4 g).

Aufarbeitung

concentrationThe reaction mixture was concentrated under reduced pressure
customto give crystalline residue, which
customto yield yellow crystals, which
customwere separated by filtration
washwashed with water
customdried
customRecrystallization from N,N-dimethylformamide

Quellen und Nachweise

ORD-Eintrag: ord-f86340e4aa114cdf8631ff2d2ef87780
Quelldatensatz: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04377580

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