Diethyl (ethoxymethylene)malonate → HCID 178469768, Verbindung

In ethanol (40 mL) was placed t-butylcarbamidine hydrochloride (3.71 g, 27.2 mmol). This was treated with 21% sodium ethoxide in ethanol (8.80 g, 27.2 mmol) and stirred at RT for 15 min. To this was added the diethyl ethoxymethylenemalonate (5.87 g, 27.2 mmol) and the reaction mixture was stirred overnight at RT. The reaction mixture was refluxed for 1 hour and then cooled to RT. The solution was evaporated, the residue dissolved in water (100 mL) and the pH adjusted to 3-4 (wet litmus) with acetic acid. The mixture formed a precipitate. The solid collected by filtration, washed with water (50 mL) and dried in vacuo to obtain ethyl 2-tert-butyl-4-hydroxypyrimidine-5-carboxylate (2.18 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 12.6 (brs, 1H), 8.44 (s, 1H), 4.20 (q, J=7.2 Hz, 2H), 1.25 (s, 9H), 1.23 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 225.0 (M+H+).

1. stirringthe reaction mixture was stirred overnight at RT
2. temperatureThe reaction mixture was refluxed for 1 hour
3. temperaturecooled to RT
4. customThe solution was evaporated
5. dissolutionthe residue dissolved in water (100 mL)
6. customThe mixture formed a precipitate
7. filtrationThe solid collected by filtration
8. washwashed with water (50 mL)
9. customdried in vacuo

ORD-Eintrag

ord-d3a2b9334cb847d9ad63b01db73f2fe6

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08143293B2