Synthesis of 3-(4-Chloro-2-methoxy-7H-pyrrolo[2,3-d]-pyrimidin-7-yl)propanoic acid – An N(9)-Functionalized 7-Deazapurine
نویسنده
چکیده
Regioselective N-alkylation of 4-chloro-2-methoxy-7H-pyrrolo[2,3d]pyrimidine (6) with ethyl 3-bromopropionate under liquid-liquid phase-transfer reaction conditions gave the ester 7a. Its saponification yielded the acid 7b. The logP values of a series of N(9)-functionalized purines and purine isosteres were calculated.
منابع مشابه
Synthesis of certain pyrrole derivatives as antimicrobial agents.
In an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis and in vitro microbiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivative...
متن کامل5-Chloro-N-[2-(1H-imidazol-4-yl)ethyl]-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
The title compound, C(12)H(13)ClN(6), was prepared by reaction of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine with 2-(1H-imid-azol-4-yl)-N-methyl-ethanamine, and the X-ray study confirmed that chloro-substituent in six-membered ring was replaced in the reaction. The exocyclic N atom environment is approximately coplanar with the pyrrolo[2,3-d]pyrimidine [corresponding dihedral angle is 5.5 (1)°], ...
متن کاملA Simple and Convenient Synthesis of Isolated-Fused Heterocycles Based on: 2-Imino-N-phenyl-2H-chromene-3-carboxamide
Starting from 2-imino-N-phenyl-2H-chromene-3-carbox-amide, (1) a series of functionalized chromenes were achieved; such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one (2), and 2-hydrazinyl-2,3-dihydro-3-phenylchromeno-[2,3-d]pyrimidin-4-one (3). Furthermore, reactions of (3) with some of laboratory available compounds gave pyrazoles (4 9, 12, 13a, 13b), tetrazoles (11), 2-(2-be...
متن کاملSynthesis and photophysical characterisation of new fluorescent triazole adenine analogues.
Fluorescent nucleic acid base analogues are powerful probes of DNA structure. Here we describe the synthesis and photo-physical characterisation of a series of 2-(4-amino-5-(1H-1,2,3-triazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl) and 2-(4-amino-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) analogues via Sonogashira cross-coupling and [3 + 2]-cycloaddition reactions as the key step...
متن کاملSynthesis of New 3-Heteroarylindoles as Potential Anticancer Agents.
2-(3-(1H-Indol-3-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-substituted-5-(substituted diazenyl)thiazoles and 2-(1H-indol-3-yl)-9-substituted-4,7-disubstituted pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(7H)-ones were synthesized via reaction of hydrazonoyl halides with each of 3-(1H-indol-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and 7-(1H-indol-3-yl)-2- thioxo-5-substi...
متن کامل