A method for the synthesis of 17-pyrimidinylandrostane

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 59; no. 8; pp. 614 - 617
• Main Authors: Komkov, Alexander V., Menchikov, Leonid G., Dmitrenok, Andrey S., Zavarzin, Igor V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.08.2023; Springer Nature; Springer; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry, Organic; Organic Chemistry; Pharmacy; Physical Sciences; Science & Technology; Synthesis; condensation; 17-pyrimidinylandrostanes; 16α,17α-epoxyandrosten-5-enes; dimethylformamide dimethyl acetal; ANTICANCER; STEROIDS; PYRIMIDINE; 16 alpha,17 alpha-epoxyandrosten-5-enes; DERIVATIVES
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-023-03241-8

A convenient synthesis method for new 17-pyrimidinylandrostanes based on 3β-hydroxy-17-[3-dimethylamino)acryloyl]-16α,17α- epoxyandrost-5-ene is proposed. The reaction of the epoxyandrostene with guanidine and acetamidine yielded 3β-hydroxy-17-(pyrimidin- 4-yl)-16α,17α-epoxyandrost-5-enes, and its reaction with 3-aminopyrazole or 3-amino-1,2,4-triazole resulted in the formation of the respective 3β-hydroxy-17-(pyrazolo[1,5- a ]pyrimidin-7-yl)-16α,17α-epoxyandrost-5-ene and 3β-hydroxy-17-(1,2,4-triazolo[1,5- a ]- pyrimidin-5-yl)-16α,17α-epoxyandrost-5-ene.