Diethyl (ethoxymethylene)malonate → HCID 178469753, compound

Participants

Reaction Steps

The title compound was prepared by (a) reaction of diethyl ethoxymethylenemalonate (11 g, 52 mmol) with phenylacetamidine (8 g, 60 mmol) to afford 40% of ethyl 2-benzyl-4-hydroxypyrimidine-5-carboxylate in analogy to Example 15, (b) reaction of 2-benzyl-4-hydroxypyrimidine-5-carboxylate (3 g, 12 mmol) with POCl3 (18 g, 116 mmol) to afford 45% of 2-benzyl-4-chloropyrimidine-5-carboxylate in analogy to Example 7, (c) reaction of 2-benzyl-4-chloropyrimidine-5-carboxylate (1.5 g, 5.5 mmol) with hydrazine (0.5 g, 16 mmol) to afford 75% of 2-benzyl-4-hydrazinopyrinmidine-5-carboxylate in analogy to Example 18, (d) reaction of ethyl 2-benzyl-4-hydrazinopyrimidine-5-carboxylate (1 g, 3.5 mmol) with citraconic anhydride (1 g, 11 mmol), in analogy to Example 21, to afford 70% (0.9 g) of the title compound; m.p. 117-118° C.

Provenance & Evidence