Formamidine acetate → 4-(Dimethoxymethyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of (3E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (C10) (147 g, 0.85 mol) and formamidine acetate (131 g, 1.26 mol) was heated at 110-120° C. for 4 hours. After cooling to room temperature, the reaction was poured into water (250 mL) and extracted with chloroform (5×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation of the residue under vacuum afforded the product as an oil. Yield: 84 g, 0.54 mol, 64%. Boiling point: 45-50° C./0.2 torr. NMR data was obtained using the product of a reaction run under similar conditions. 1H NMR (400 MHz, CDCl3) δ 3.30 (s, 6H), 5.21 (s, 1H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 8.68 (d, J=5.1 Hz, 1H), 9.12 (d, J=1.4 Hz, 1H).

Provenance & Evidence