Diethyl (ethoxymethylene)malonate → HCID 178469768, compound

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 and the residue was 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 under vacuum 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, 1 H), 8.44 (s, 1 H), 4.20 (q, J=7.2 Hz, 2 H), 1.25 (s, 9 H), 1.23 (t, J=12 Hz, 3 H); 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 was 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 under vacuum

ORD record

ord-41b7bce74bf24c12a482849e75f89d12

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188113B2