Synthesizing Viagra

Chem project...OBVIOUSLY I am NOT a chemist but I did the best I could. First time doing an animation of this sort too :)

This is the long-winded version for presentation purposes.

Sildenafil (Viagra(TM)), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction

The methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester (I) with hot dimethyl sulfate gives 1-methyl-3-propylpyrazole-5-carboxylic acid ethyl ester (II), which is hydrolyzed with aqueous NaOH to the corresponding free acid (III). The nitration of (III) with oleum/fuming nitric acid yields the 4-nitro derivative (IV), which is treated first with refluxing SOCl2 and then with NH4OH to afford the corresponding carboxamide (V). The reduction of the nitro group of (V) with SnCl2 dihydrate in refluxing ethanol gives 4-amino-1-methyl-3-propylpyrazole-5-carboxamide (VI), which is acylated with 2-ethoxybenzoyl chloride (VII) by means of triethylamine in dichloromethane yielding 4-(2-ethoxybenzamido)-1-methyl-3-propylpyrazole-5-carboxamide (VIII). The cyclization of (VIII) by means of NaOH and H2O2 in refluxing ethanol affords 5-(2-ethoxyphenyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d] pyrimidin-7-one (IX), which is sulfonated with chlorosulfonic acid affording the chlorosulfonyl derivative (X). Finally, this compound is condensed with 1-methylpiperazine in ethanol at room temperature.




Credits
Bioorg Med Chem Lett
http://www.chemdrug.com/databases/8_0_iyiqedtwdmhtgeof.html

Category:

Science & Technology

Tags:

• Synthesizing
• Viagra

[UBUIBME86]

@psmanici4

LOL...it was a hoot during the presentation..well worth the effort and humor!

[psmanici4]

Good job man, but id be petrified of my tutor if i came up with mechanisms like that infront of him haha :P.