Sodium Hydroxide → HCID 21220605, compound

Participants

Reaction Steps

The title compound was prepared by (a) reaction of ethyl propionylacetate (19.4 g, 0.13 mol) and N,N-dimethylformamide dimethyl acetal (16.0 g, 0.13 mol) in analogy to Example 67, (b) reaction with NaOEt (0.18 mol) and S-methyl isothouronium sulfate (18.7 g, 0.067 mol) also described for Example 67, (c) hydrolysis of the ethyl 4-ethyl-2-methylthiopyrimidine-5-carboxylate (18.0 g, 0.08 mmol) with NaOH (12.7 g, 0.32 mol) in H2O (200 mL) as described in Example 67, (d) reaction of the 4-ethyl-2-methylthiopyrimidine-5-carboxylic acid (0.50 g, 2.5 mmol) and oxalyl chloride (0.32 g, 2.5 mmol) as described in Example 11, and (e) reaction of the 4-ethyl-2-methylthiopyrimidine-5-carbonyl chloride (0.50 g, 2.3 mmol) and phenyl magnesium bromide as described for Example 23, resulting in a yield of 22% (0.14 g) from the 4-ethyl-2-methylthiopyrimidine-5-carboxylic acid;); 1H NMR (CDCl3) δ 9.18 (s, 1H), 7.80 (d, 2H), 7.62 (t, 1H), 7.50 (t, 2H), 2.81 (q, 2H), 2.61 (s, 3H), 1.22 (t, 3H).

Provenance & Evidence