Carbonic acid-guanidine (1:1) → 2-amino-6-(diethoxymethyl)pyrimidin-4(3H)-one

HRID 7634

Reaktionsgleichung

Reaktionsgleichung von HRID 7634
C([O:3][C:4](=O)[CH2:5][C:6](=O)[CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])C.C(=O)(O)O.[NH2:20][C:21]([NH2:23])=[NH:22]>C(O)C>[NH2:22][C:21]1[NH:23][C:4](=[O:3])[CH:5]=[C:6]([CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[N:20]=1

Komponenten

4

Edukt 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Produkt 1

HCID 1353994012-amino-6-(diethoxymethyl)pyrimidin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4,4-diethoxy-3-oxo-butyric acid ethyl ester [Johnson, T. B. and Mikeska, L. A. J. Am. Chem. Soc. 41, 810 (1919)] (18.0 g, 82.5 mol) in ethanol (300 mL) was treated with guanidine carbonate (14.8 g, 82.5 mol) and this was stirred under reflux until no solid remained (˜4 hours). The mixture was concentrated, diluted with water and the solid was collected by filtration to give D1.1 (13.1 g, 74%) as a beige solid. 1H-NMR (DMSO-d6) δ: 10.78 (1H, br s), 6.61 (2H, br s), 5.63 (1H, s), 4.90 (1H, s), 3.51 (4H, m), 1.13 (6H, t, J=7.1 Hz). LC/MSc: ret. time: 0.757 min. (M+H)+: 214. M.p.: 198.0–202.7° C.

Aufarbeitung

  1. temperatureunder reflux until no solid
  2. custom(˜4 hours)
  3. concentrationThe mixture was concentrated
  4. additiondiluted with water
  5. filtrationthe solid was collected by filtration
  6. customto give D1.1 (13.1 g, 74%) as a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-083c6a63c5cf4ef4a1d50b8a2e104444
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087614B2

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