Guanidine → Diaveridine

Participants

Reaction Steps

Veratric acid is esterified by refluxing in methanol using hydrochloric acid as catalyst. The resulting methyl 3,4-dimethoxybenzoate is converted under the conditions of Example 103 to ω-(methylsulfinyl) 3,4-dimethoxyacetophenone. This is reduced with sodium borohydride under the condition of Example 104 to β-hydroxy-β-(3,4-dimethoxyphenyl)ethyl methyl sulphoxide, which is then allowed to react with β-anilinopropionitrile in hexamethylphosphoramide containing sodium methylate according to Example 105. The resulting α-(3,4-dimethoxybenzyl)-β-anilinoacrylonitrile is condensed with guanidine according to Example 106 to give 2,4-diamino-5-(3',4'-dimethoxybenzyl) pyrimidine, m.p. 224°-229° C.

Provenance & Evidence