Reaktion #483452

Reaktionsgleichung

1,3-bis(cyclohexylmethyl)-5,6-diaminouracil

5-(methoxycarbonyl)pyridine-2-carboxylic acid

diisopropylethylamine

→

6-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)nicotinic Acid

Ausbeute 71.4%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure
2. 2
   Temperaturheated
3. 3
   Temperaturto reflux for 3 hours
4. 4
   TemperaturThe reaction mixture was cooled to room temperature
5. 5
   workup.ADDITIONdiluted with acetic acid
6. 6
   Sonstigethe product precipitated from the reaction mixture

Vorschrift

To 1,3-bis(cyclohexylmethyl)-5,6-diaminouracil (1.45 g, 4.33 mmol), from Example 1, part (d) above, in dichloromethane (25 mL) was added the intermediate 5-(methoxycarbonyl)pyridine-2-carboxylic acid (1.78 g, 5.52 mmol) and diisopropylethylamine (Aldrich, 0.84 g, 6.5 mmol). This reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the crude material was taken up in 1N sodium hydroxide and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, diluted with acetic acid and the product precipitated from the reaction mixture to provide 6-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)nicotinic Acid (1.44 g, 56%) as a green solid. 1H-NMR (300 MHz, DMSO-d6) δ: 9.68 (s, 1H), 9.10 (d, J=3.1 Hz, 1H), 8.43 (m, 1H), 8.12 (m, 1H), 6.71 (br s, 1H), 4.12-3.60 (br m, 4H), 1.80-1.40 (m, 11H), 1.35-0.91 (m, 11H).

Quelle