Abstract: The synthesis of steroidal heterocycles containing the pyrazole and pyrimidine ring fused to the 16,17-position of the steroid nucleus is reported. Androstenolone acetate (1) reacted with carbon disulfide, iodomethane and sodium hydride to furnish 3β-acetoxy-16-[bis(methylthio)methylene]-5-androst-5-en-17-one (2). The reactions of 2 with hydrazine hydrate and methylhydrazine afforded the 5’-methylthio- pyrazolo[4’,3’:16,17]androst-5-en-3β-ols 3a and 3b, respectively. Treatment of 2 with amidinium, guanidinium, and isothiuronium salts in the presence of sodium methoxide yielded the 6’-methoxy-pyrimido[5’,4’:16,17]androst-5-en-3β-ols (4a-4e).
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Rivera, D.G.; Peseke, K.; Jomarrón, I.; Montero, A.; Molina, R.; Coll, F. Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives. Molecules 2003, 8, 444-452.
Rivera DG, Peseke K, Jomarrón I, Montero A, Molina R, Coll F. Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives. Molecules. 2003; 8(5):444-452.
Rivera, Daniel G.; Peseke, Klaus; Jomarrón, Isabel; Montero, Alina; Molina, Reinaldo; Coll, Francisco. 2003. "Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives." Molecules 8, no. 5: 444-452.