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6-Methoxy-2-methylpyrimidin-4-amine → (7-Methoxy-5-methylimidazo[2,1-f]pyrimidin-2-yl)-phenylmethanone

HRID 236289
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 236289
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.Br[CH2:12][C:13](=O)[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>O1CCCC1.CCOCC>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]2[CH:12]=[C:13]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[N:10]=[C:5]2[CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 5494356-Methoxy-2-methylpyrimidin-4-amineHCID 125689113-Bromo-1-phenylpropane-1,2-dione

Produkt 1

HCID 13478385(7-Methoxy-5-methylimidazo[2,1-f]pyrimidin-2-yl)-phenylmethanoneAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 2.1 g of 6-methoxy-2-methyl-4-pyrimidinamine in dry tetrahydrofuran was treated with a solution of 5.4 g of 3-bromo-1-phenyl-1,2-propanedione in 5 ml of dry ether. After stirring overnight, the mixture was chilled and the precipitated salt filtered off. A suspension of the salt in dry ethanol was refluxed for 1.5 hours, chilled, and filtered. The solid was shaken with a mixture of chloroform and aqueous sodium bicarbonate and the organic layer was evaporated to dryness under reduced pressure. The residue was chromatographed in ethyl acetate on silica to obtain 2.7 g of (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl)-phenylmethanone as a yellow crystalline solid melting at 165°-7° C.

Aufarbeitung

  1. temperaturethe mixture was chilled
  2. filtrationthe precipitated salt filtered off
  3. additionA suspension of the salt in dry ethanol
  4. temperaturewas refluxed for 1.5 hours
  5. temperaturechilled
  6. filtrationfiltered
  7. stirringThe solid was shaken with a mixture of chloroform and aqueous sodium bicarbonate
  8. customthe organic layer was evaporated to dryness under reduced pressure
  9. customThe residue was chromatographed in ethyl acetate on silica

Quellen und Nachweise

ORD-Eintrag
ord-1a4a3f0f49234fa5b11d092a5cc62dcc
Quelldatensatz
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04643999

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