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CAS 23356-96-9
(S)-pyrrolidin-2-ylmethanol
Codes: AVAN-008
Application context (from source-drug indications)
Erectile dysfunctionAvanafil
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Avanafil | Tier C — Watch / trade | 2028 |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
diethyl 2-(ethoxymethylene)malonate→methyl carbamimidothioate→ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate→ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate→(3-chloro-4-methoxyphenyl)methanamine hydrochloride→ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate→ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate→(S)-pyrrolidin-2-ylmethanol→ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate→(S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid→pyrimidin-2-ylmethanamine hydrochloride
ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate→ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate→(S)-pyrrolidin-2-ylmethanol→(3-chloro-4-methoxyphenyl)methanamine→4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid→pyrimidin-2-ylmethanamine→4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
(S)-pyrrolidin-2-ylmethanol→4-(bromomethyl)-2-chloro-1-methoxybenzene→4-aminopyrimidin-2(1H)-one→4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2(1H)-one→(S)-(1-(4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2-yl)pyrrolidin-2-yl)methanol→N-(pyrimidin-2-ylmethyl)formamide
(S)-pyrrolidin-2-ylmethanol→4-(bromomethyl)-2-chloro-1-methoxybenzene→4-aminopyrimidin-2(1H)-one→4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2(1H)-one→N-(pyrimidin-2-ylmethyl)formamide→4-((3-chloro-4-methoxybenzyl)amino)-2-oxo-N-(pyrimidin-2-ylmethyl)-1,2-dihydropyrimidine-5-carboxamide
(S)-pyrrolidin-2-ylmethanol→(3-chloro-4-methoxyphenyl)methanamine→pyrimidin-2-ylmethanamine→2,4-dichloropyrimidine-5-carbonyl chloride→4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride→2,4-bis(methylthio)pyrimidine-5-carbonyl chloride→4-bromo-2-(methylthio)pyrimidine-5-carbonyl chloride→4-chloro-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→2,4-dichloro-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→2,4-bis(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→4-chloro-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→2-chloro-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide→4-bromo-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
diethyl 2-(ethoxymethylene)malonate→(3-chloro-4-methoxyphenyl)methanamine hydrochloride→(S)-pyrrolidin-2-ylmethanol→pyrimidin-2-ylmethanamine→thiourea→AVAN-027→AVAN-028→AVAN-029→AVAN-030→AVAN-031→AVAN-032→AVAN-033
(S)-pyrrolidin-2-ylmethanol→ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate→pyrimidin-2-ylmethanamine→ethyl 2-cyanoacetate→urea→ethyl (E)-2-cyano-3-ureidoacrylate→ethyl 6-amino-2-oxo-1,2-dihydropyrimidine-5-carboxylate→2-chloro-4-(chloromethyl)-1-methoxybenzene→ethyl 6-((3-chloro-4-methoxybenzyl)amino)-2-oxo-1,2-dihydropyrimidine-5-carboxylate
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