Acetic Anhydride → HCID 136109365, Verbindung

HRID 1638596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638596
[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[CH2:5][CH2:6][C:7]1[C:12](=[O:13])[NH:11][C:10]([NH2:14])=[N:9][C:8]=1[NH2:15])[CH3:2].C(O[C:23](=[O:25])[CH3:24])(=O)C>N1C=CC=CC=1>[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[CH2:5][CH2:6][C:7]1[C:12](=[O:13])[NH:11][C:10]([NH:14][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[N:15]([C:23](=[O:25])[CH3:24])[C:12](=[O:13])[CH3:7])[CH3:2]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 135816675HCID 135816675, Verbindung

Produkt 1

HCID 136109365HCID 136109365, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A stirred mixture of 7.20 g (28.1 mmol) of 3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde diethyl acetal, 30 ml of dry pyridine and 30 ml of freshly distilled acetic anhydride was heated on an oil bath at 90° for 6 hours and then stirred at ambient temperature overnight. Solution occurred within 15 minutes as a mixture of diacetyl and triacetyl pyrimidinone formed; extended reaction was required to obtain only the title compound. The solution was spin evaporated in vacuo to give an oil. Ethyl acetate was added and spin evaporated several times until a solid was obtained. The solid was dispersed in cyclohexane and collected; yield, 8.88 g (82%), mp 126°-137° (one spot on TLC). Recrystallization of a portion from cyclohexane-ethylacetate gave the analytical sample, mp 138°-139° ; TLC (C6H6 :EtOH/5:1); NMR (DMSO-d6)δ1.08 (t, 6H, 2CH2CH3), 1.63 (m, 2H, CH2CH 2CH), 2.13 (s, 3H, Ac), 2.27 (s, 6H, 2Ac), 2.2 (2H, CH2CH, superimposed on the acetyl singlets), 3.2-3.7 (m, 4H, 2 x OCH2), 4.42 (t, 1H, CH), 11.87 (br s, 2H, AcNH and HNC(0)).

Aufarbeitung

  1. temperaturewas heated on an oil bath at 90° for 6 hours
  2. customformed
  3. customextended reaction

Quellen und Nachweise

ORD-Eintrag
ord-8836346ca6fa4a0689ecfd59e7b34803
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880812

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