Diethyl Ether → HCID 178441842, Verbindung

HRID 486027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486027
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10](C(OC)=O)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[CH3:20][Mg]Br.C([O:25][CH2:26][CH3:27])C>O1CCCC1.O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:26]([OH:25])([CH3:27])[CH3:20])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 178418573HCID 178418573, VerbindungHCID 178441861methyl 2-butyl-4-oxo-1H-quinazoline-6-carboxylate

Produkt 1

HCID 178441842HCID 178441842, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 0.075 g of methyl 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxylate in 5 ml of dry tetrahydrofuran, cooled to 0° C., is added dropwise 0.51 ml of a solution of 3.0M methylmagnesium bromide in diethyl ether. The reaction is stirred at 0° C. for 0.5 hours and then at room temperature for 1 hour followed by quenching with 10 ml of saturated ammonium chloride solution. The resulting reaction mixture is diluted with 10 ml of water and extracted with ethyl acetate. The combined organics are dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 100:0.25 chloroform-methanol to yield 0.055 g of the desired product as a white solid, m.p. 190°-192° C.

Aufarbeitung

  1. waitat room temperature for 1 hour followed
  2. customby quenching with 10 ml of saturated ammonium chloride solution
  3. customThe resulting reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organics are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica gel
  9. washeluting with 100:0.25 chloroform-methanol

Quellen und Nachweise

ORD-Eintrag
ord-8cc9bfa632c04e2395bddc5a1140ea28
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290780

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