SYNTHESIS OF 7-ARYLMETHYL-SUBSTITUTED DERIVATIVES OF 2-AMINO-2-PYRROLYDIN-1-YL-5,6,7,8-TETRAHYDROPYRIDO[3,4-<i.d</i>]PYRIMIDINE

Authors

  • А. Ю. Кузнецов nstitute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka 142432, Moscow Region
  • С. В. Чапышев nstitute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka 142432, Moscow Region

DOI:

https://doi.org/10.1007/7399

Keywords:

1-benzyl-4-ethoxycarbonyl-3-oxopiperidine, pyrido[3, 4-d]pyrimidines, pyrrolidine-1-carboxamidine, sodium triacetoxyborohydride, reductive amination, condensation

Abstract

7-Benzyl-2-pyrrolidin-1-yl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one was prepared by condensation of 1-benzyl-4-ethoxycarbonyl-3-oxopiperidine with pyrrolidine-1-carboxamidine. Subsequent treatment of the product with  trifluoromethansulfonyl anhydride, aqueous ammonia, and hydrogen  in  the  presence of palladium on carbon gave 4-amino-2-pyrrolidin-1-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine in 80% yield.  The given compound was used in the reductive amination of aldehydes in the synthesis of various 7-arylmethyl-substituted derivatives of  4-amino-2-pyrrolidin-1-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine.

How to Cite
Kuznetsov, A. Yu.; Chapyshev, S. V.  Chem. Heterocycl. Compd. 2007, 43, 1167. [Khim. Geterotsikl. Soedin. 2007, 1374.]

For this article in the English edition see DOI 10.1007/s10593-007-0179-6


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Published

2023-01-30

Issue

No. 9 (2007)

Section

Original Papers