Synthesis of 2,4-Di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indoles, Including Antiasthma Clinical Candidate PNU-142731A

Two syntheses are described for 1-[(2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indol-9-yl)-acetyl]pyrrolidine hydrochloride (PNU-142731A), a clinical candidate in the asthma area. The route involving the initial regioselective addition of glycine ethyl ester to commercially available 2,4,6-trichloropyr...

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Published in:Organic process research & development 2001-03, Vol.5 (2), p.144-151
Main Authors: Bundy, Gordon L, Banitt, Lee S, Dobrowolski, Paul J, Palmer, John R, Schwartz, Theresa M, Zimmermann, David C, Lipton, Michael F, Mauragis, Michael A, Veley, Michael F, Appell, Robert B, Clouse, Robert C, Daugs, Edward D
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Language:English
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Summary:Two syntheses are described for 1-[(2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indol-9-yl)-acetyl]pyrrolidine hydrochloride (PNU-142731A), a clinical candidate in the asthma area. The route involving the initial regioselective addition of glycine ethyl ester to commercially available 2,4,6-trichloropyrimidine is particularly well-suited for large-scale operation, as it is short, proceeds in good yield, is operationally straightforward, and requires no chromatographic purification of intermediates.
ISSN:1083-6160
1520-586X
DOI:10.1021/op000221p