Dimethyl methoxymethylenemalonate → HCID 178498799, compound

Participants

Reaction Steps

Pivalamidine hydrochloride (5.00 g, 37 mmol) dissolved in methanol (80 mL) was treated with NaOMe (2.0 g, 37 mmol) and stirred at RT for 15 min. To this was added dimethyl 2-(methoxymethylene)malonate (6.4 g, 37 mmol) and the solution stirred at RT overnight. The solution was heated at reflux for 1 h, then cooled to RT and concentrated. The oily mass was dissolved in H2O (125 mL) and the pH adjusted to ˜3 (wet litmus) with AcOH. The precipitated solids were collected by filtration, washed with H2O (50 mL) and dried to yield methyl 2-t-butyl-4-hydroxypyrimidine-5-carboxylate (3.50 g, 45%). 1H NMR (400 MHz, DMSO-d6): δ 1.29 (s, 9H), 2.97 (s, 3H), 8.47 (s, 1H).

Provenance & Evidence